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The title compound, [Cr{1,3-(MeO)2C6H4}(CO)3], exhibits the three-legged piano stool structure expected for a metal tri­carbonyl with an η6-coordinated arene. Two independent mirror-symmetric mol­ecules are found in the unit cell. The methoxy groups display an out-of-plane distortion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804005914/om6225sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804005914/om6225Isup2.hkl
Contains datablock I

CCDC reference: 238660

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.031
  • wR factor = 0.089
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size ....... 0.82 mm
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 12 PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C6 .. 5.42 su PLAT230_ALERT_2_C Hirshfeld Test Diff for O3 - C7 .. 6.92 su PLAT230_ALERT_2_C Hirshfeld Test Diff for O2' - C6' .. 6.43 su PLAT230_ALERT_2_C Hirshfeld Test Diff for O3' - C7' .. 5.08 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr1 - C6 .. 8.44 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr1 - C7 .. 8.87 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr2 - C6' .. 9.35 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr2 - C7' .. 6.97 su
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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, 1997–2000); cell refinement: SAINT-Plus (Bruker, 1997–1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
[Cr(C8H10O2)(CO)3]Dx = 1.792 Mg m3
Mr = 274.19Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PnmaCell parameters from 6108 reflections
a = 11.5948 (19) Åθ = 2.2–28.2°
b = 13.440 (2) ŵ = 1.13 mm1
c = 13.046 (2) ÅT = 273 K
V = 2033.0 (6) Å3Plate, yellow
Z = 80.82 × 0.16 × 0.02 mm
F(000) = 1120
Data collection top
Bruker AXS SMART APEX CCD
diffractometer
2549 independent reflections
Radiation source: fine-focus sealed tube1983 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
ω scansθmax = 28.2°, θmin = 2.2°
Absorption correction: multi scan
(SADABS in SAINT-Plus; Bruker, 1997–1999)
h = 1515
Tmin = 0.779, Tmax = 0.980k = 1717
12064 measured reflectionsl = 1711
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)] = 0.031Hydrogen site location: difference Fourier map
wR(F2) = 0.089Only H-atom coordinates refined
S = 1.04 w = 1/[σ2(Fo2) + (0.0454P)2 + 1.1678P]
where P = (Fo2 + 2Fc2)/3
2549 reflections(Δ/σ)max = 0.001
213 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.46 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
Cr20.67754 (4)0.75000.21188 (3)0.01490 (13)
O1'0.76133 (12)0.58175 (10)0.05199 (11)0.0194 (3)
O3'0.5301 (2)0.75000.39265 (17)0.0266 (5)
O2'0.81384 (14)0.59562 (12)0.31212 (13)0.0306 (4)
C7'0.5859 (3)0.75000.3218 (2)0.0201 (6)
C6'0.76175 (18)0.65560 (16)0.27308 (17)0.0210 (4)
C1'0.7564 (3)0.75000.0599 (2)0.0168 (6)
C3'0.58465 (18)0.66067 (16)0.09900 (15)0.0183 (4)
C4'0.5302 (3)0.75000.1138 (2)0.0185 (6)
C2'0.69825 (18)0.66134 (14)0.06979 (15)0.0171 (4)
Cr10.56343 (4)0.25000.22131 (3)0.01391 (13)
O30.70808 (19)0.25000.03840 (16)0.0226 (5)
O10.48340 (13)0.41768 (10)0.38540 (11)0.0203 (3)
O20.43143 (13)0.40955 (11)0.12512 (12)0.0238 (3)
C40.7122 (3)0.25000.3162 (2)0.0181 (6)
C10.4885 (3)0.25000.3762 (2)0.0176 (6)
C70.6533 (3)0.25000.1101 (2)0.0187 (6)
C20.54581 (18)0.33848 (14)0.36516 (15)0.0179 (4)
C60.48110 (18)0.34698 (15)0.16182 (16)0.0180 (4)
C30.65849 (18)0.33934 (16)0.33244 (16)0.0179 (4)
C50.5320 (2)0.51133 (16)0.36531 (19)0.0244 (5)
C5'0.7107 (2)0.48869 (16)0.0706 (2)0.0240 (5)
H1A0.416 (3)0.25000.400 (3)0.029*
H1B0.835 (3)0.75000.048 (3)0.029*
H4B0.454 (3)0.75000.145 (3)0.029*
H4A0.786 (3)0.25000.289 (3)0.029*
H3A0.700 (2)0.3999 (19)0.326 (2)0.029*
H5C0.479 (2)0.554 (2)0.384 (2)0.036*
H3B0.548 (2)0.5998 (19)0.1067 (19)0.029*
H5F0.764 (2)0.444 (2)0.063 (2)0.036*
H5E0.685 (2)0.483 (2)0.139 (2)0.036*
H5B0.602 (2)0.522 (2)0.407 (2)0.036*
H5D0.648 (2)0.478 (2)0.025 (2)0.036*
H5A0.550 (2)0.519 (2)0.292 (2)0.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cr20.0159 (2)0.0136 (2)0.0151 (2)0.0000.00013 (17)0.000
O1'0.0222 (7)0.0126 (7)0.0234 (8)0.0001 (6)0.0034 (6)0.0006 (6)
O3'0.0299 (12)0.0271 (12)0.0228 (12)0.0000.0097 (10)0.000
O2'0.0331 (9)0.0227 (8)0.0361 (10)0.0066 (7)0.0090 (7)0.0048 (7)
C7'0.0229 (15)0.0144 (14)0.0231 (16)0.0000.0028 (12)0.000
C6'0.0219 (10)0.0201 (10)0.0211 (11)0.0034 (9)0.0009 (8)0.0030 (8)
C1'0.0191 (14)0.0163 (13)0.0151 (14)0.0000.0011 (11)0.000
C3'0.0203 (10)0.0179 (10)0.0167 (10)0.0026 (8)0.0008 (8)0.0009 (8)
C4'0.0155 (14)0.0231 (15)0.0167 (14)0.0000.0007 (11)0.000
C2'0.0203 (10)0.0165 (9)0.0145 (9)0.0001 (8)0.0001 (8)0.0010 (7)
Cr10.0135 (2)0.0132 (2)0.0150 (2)0.0000.00073 (17)0.000
O30.0220 (11)0.0244 (11)0.0213 (12)0.0000.0068 (9)0.000
O10.0224 (8)0.0133 (7)0.0251 (8)0.0006 (6)0.0044 (6)0.0017 (6)
O20.0272 (8)0.0181 (8)0.0263 (8)0.0063 (6)0.0045 (7)0.0008 (6)
C40.0129 (14)0.0243 (15)0.0171 (14)0.0000.0041 (10)0.000
C10.0203 (15)0.0189 (14)0.0135 (13)0.0000.0017 (11)0.000
C70.0187 (14)0.0124 (13)0.0250 (16)0.0000.0050 (12)0.000
C20.0216 (10)0.0163 (10)0.0156 (10)0.0009 (8)0.0026 (8)0.0016 (7)
C60.0178 (10)0.0182 (10)0.0180 (10)0.0024 (8)0.0003 (8)0.0031 (8)
C30.0173 (10)0.0182 (10)0.0182 (10)0.0029 (8)0.0031 (8)0.0002 (8)
C50.0287 (13)0.0145 (10)0.0302 (13)0.0026 (9)0.0025 (10)0.0009 (9)
C5'0.0273 (12)0.0139 (10)0.0307 (13)0.0025 (9)0.0009 (10)0.0023 (9)
Geometric parameters (Å, º) top
Cr2—C7'1.784 (3)Cr1—C42.123 (3)
Cr2—C6'i1.789 (2)Cr1—C32.181 (2)
Cr2—C6'1.789 (2)Cr1—C3ii2.181 (2)
Cr2—C4'2.135 (3)Cr1—C12.200 (3)
Cr2—C1'2.184 (3)Cr1—C22.231 (2)
Cr2—C3'2.184 (2)Cr1—C2ii2.231 (2)
Cr2—C3'i2.184 (2)O3—C71.131 (4)
Cr2—C2'2.217 (2)O1—C21.314 (2)
Cr2—C2'i2.217 (2)O1—C51.404 (2)
O1'—C2'1.316 (2)O2—C61.126 (2)
O1'—C5'1.403 (2)C4—C3ii1.369 (3)
O3'—C7'1.129 (4)C4—C31.369 (3)
O2'—C6'1.129 (3)C4—H4A0.93 (4)
C1'—C2'1.375 (2)C1—C21.370 (2)
C1'—C2'i1.375 (2)C1—C2ii1.370 (2)
C1'—H1B0.93 (4)C1—H1A0.89 (4)
C3'—C4'1.370 (3)C2—C31.374 (3)
C3'—C2'1.371 (3)C3—H3A0.95 (3)
C3'—H3B0.93 (3)C5—H5C0.87 (3)
C4'—C3'i1.370 (3)C5—H5B0.98 (3)
C4'—H4B0.98 (4)C5—H5A0.98 (3)
Cr1—C71.786 (3)C5'—H5F0.87 (3)
Cr1—C6ii1.792 (2)C5'—H5E0.95 (3)
Cr1—C61.792 (2)C5'—H5D0.95 (3)
C7'—Cr2—C6'i88.08 (10)C7—Cr1—C3104.17 (10)
C7'—Cr2—C6'88.08 (10)C6ii—Cr1—C3163.17 (9)
C6'i—Cr2—C6'90.34 (13)C6—Cr1—C399.01 (8)
C7'—Cr2—C4'90.28 (13)C4—Cr1—C337.07 (7)
C6'i—Cr2—C4'134.78 (7)C7—Cr1—C3ii104.17 (10)
C6'—Cr2—C4'134.78 (7)C6ii—Cr1—C3ii99.01 (8)
C7'—Cr2—C1'168.21 (13)C6—Cr1—C3ii163.17 (9)
C6'i—Cr2—C1'100.18 (9)C4—Cr1—C3ii37.07 (7)
C6'—Cr2—C1'100.18 (9)C3—Cr1—C3ii66.80 (11)
C4'—Cr2—C1'77.93 (11)C7—Cr1—C1167.56 (12)
C7'—Cr2—C3'104.36 (10)C6ii—Cr1—C1100.80 (9)
C6'i—Cr2—C3'163.72 (9)C6—Cr1—C1100.80 (9)
C6'—Cr2—C3'100.38 (9)C4—Cr1—C177.62 (12)
C4'—Cr2—C3'36.97 (6)C3—Cr1—C165.74 (9)
C1'—Cr2—C3'66.06 (9)C3ii—Cr1—C165.74 (9)
C7'—Cr2—C3'i104.36 (10)C7—Cr1—C2137.43 (8)
C6'i—Cr2—C3'i100.38 (9)C6ii—Cr1—C2134.67 (9)
C6'—Cr2—C3'i163.72 (9)C6—Cr1—C285.86 (8)
C4'—Cr2—C3'i36.97 (6)C4—Cr1—C265.43 (9)
C1'—Cr2—C3'i66.06 (9)C3—Cr1—C236.28 (8)
C3'—Cr2—C3'i66.69 (11)C3ii—Cr1—C277.33 (8)
C7'—Cr2—C2'137.42 (8)C1—Cr1—C236.01 (6)
C6'i—Cr2—C2'134.05 (9)C7—Cr1—C2ii137.43 (8)
C6'—Cr2—C2'86.15 (9)C6ii—Cr1—C2ii85.86 (8)
C4'—Cr2—C2'65.51 (8)C6—Cr1—C2ii134.67 (9)
C1'—Cr2—C2'36.42 (6)C4—Cr1—C2ii65.43 (9)
C3'—Cr2—C2'36.30 (8)C3—Cr1—C2ii77.33 (8)
C3'i—Cr2—C2'77.59 (8)C3ii—Cr1—C2ii36.28 (8)
C7'—Cr2—C2'i137.42 (8)C1—Cr1—C2ii36.01 (6)
C6'i—Cr2—C2'i86.15 (9)C2—Cr1—C2ii64.42 (10)
C6'—Cr2—C2'i134.05 (9)C2—O1—C5117.89 (17)
C4'—Cr2—C2'i65.51 (8)C3ii—C4—C3122.5 (3)
C1'—Cr2—C2'i36.42 (6)C3ii—C4—Cr173.77 (15)
C3'—Cr2—C2'i77.59 (8)C3—C4—Cr173.77 (15)
C3'i—Cr2—C2'i36.30 (8)C3ii—C4—H4A118.69 (16)
C2'—Cr2—C2'i65.04 (10)C3—C4—H4A118.69 (17)
C2'—O1'—C5'117.47 (17)Cr1—C4—H4A122 (2)
O3'—C7'—Cr2178.4 (3)C2—C1—C2ii120.5 (3)
O2'—C6'—Cr2179.3 (2)C2—C1—Cr173.23 (15)
C2'—C1'—C2'i120.1 (3)C2ii—C1—Cr173.23 (15)
C2'—C1'—Cr273.09 (15)C2—C1—H1A119.5 (2)
C2'i—C1'—Cr273.09 (15)C2ii—C1—H1A119.5 (2)
C2'—C1'—H1B119.95 (14)Cr1—C1—H1A133 (2)
C2'i—C1'—H1B119.95 (14)O3—C7—Cr1178.4 (3)
Cr2—C1'—H1B125 (2)O1—C2—C1114.50 (19)
C4'—C3'—C2'118.4 (2)O1—C2—C3125.39 (19)
C4'—C3'—Cr269.57 (15)C1—C2—C3120.1 (2)
C2'—C3'—Cr273.15 (12)O1—C2—Cr1130.64 (14)
C4'—C3'—H3B122.8 (16)C1—C2—Cr170.76 (14)
C2'—C3'—H3B118.7 (16)C3—C2—Cr169.89 (12)
Cr2—C3'—H3B129.7 (16)O2—C6—Cr1178.28 (19)
C3'i—C4'—C3'122.4 (3)C4—C3—C2118.3 (2)
C3'i—C4'—Cr273.46 (15)C4—C3—Cr169.16 (15)
C3'—C4'—Cr273.46 (15)C2—C3—Cr173.83 (12)
C3'i—C4'—H4B118.6 (2)C4—C3—H3A120.3 (15)
C3'—C4'—H4B118.6 (2)C2—C3—H3A121.3 (15)
Cr2—C4'—H4B119 (2)Cr1—C3—H3A131.8 (16)
O1'—C2'—C3'125.27 (19)O1—C5—H5C104.7 (18)
O1'—C2'—C1'114.51 (19)O1—C5—H5B110.7 (16)
C3'—C2'—C1'120.2 (2)H5C—C5—H5B109 (2)
O1'—C2'—Cr2130.12 (14)O1—C5—H5A111.3 (16)
C3'—C2'—Cr270.55 (12)H5C—C5—H5A111 (2)
C1'—C2'—Cr270.49 (14)H5B—C5—H5A110 (2)
C7—Cr1—C6ii87.66 (9)O1'—C5'—H5F107.1 (18)
C7—Cr1—C687.66 (9)O1'—C5'—H5E111.4 (16)
C6ii—Cr1—C693.31 (13)H5F—C5'—H5E107 (2)
C7—Cr1—C489.94 (13)O1'—C5'—H5D110.4 (17)
C6ii—Cr1—C4133.25 (6)H5F—C5'—H5D111 (2)
C6—Cr1—C4133.25 (6)H5E—C5'—H5D110 (2)
Symmetry codes: (i) x, y+3/2, z; (ii) x, y+1/2, z.
 

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