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The title compound, (1,3,5-(MeO)3C6H3)Cr(CO)3 or [Cr(C9H12O3)(CO)3], exhibits the three-legged piano-stool structure expected for a metal tri­carbonyl with an η6-coordinated arene. The mol­ecule exhibits threefold symmetry. The methoxy groups display an out-of-plane distortion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024292/cv6248sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024292/cv6248Isup2.hkl
Contains datablock I

CCDC reference: 226686

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.025
  • wR factor = 0.069
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

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Alert level C 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... 1 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr1 - C4 = 8.65 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 28.40 From the CIF: _reflns_number_total 1040 Count of symmetry unique reflns 530 Completeness (_total/calc) 196.23% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 510 Fraction of Friedel pairs measured 0.962 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 3 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.

Tricarbonyl(η6-1,3,5-trimethoxybenzene)chromium(0) top
Crystal data top
[Cr(C9H12O3)(CO)3]Dx = 1.625 Mg m3
Mr = 304.22Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3cCell parameters from 5768 reflections
a = 12.6892 (9) Åθ = 2.4–28.4°
c = 13.3798 (19) ŵ = 0.94 mm1
V = 1865.7 (3) Å3T = 100 K
Z = 6Block, colourless
F(000) = 9360.56 × 0.20 × 0.16 mm
Data collection top
Bruker AXS SMART APEX CCD
diffractometer
1040 independent reflections
Radiation source: fine-focus sealed tube1038 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 28.4°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS in SAINT-Plus; Bruker, 1997-1999)
h = 1616
Tmin = 0.568, Tmax = 0.86k = 1616
5069 measured reflectionsl = 1717
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)] = 0.026H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.069 w = 1/[σ2(Fo2) + (0.0478P)2 + 0.4118P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
1040 reflectionsΔρmax = 0.54 e Å3
64 parametersΔρmin = 0.68 e Å3
1 restraintAbsolute structure: Flack (1983), 510 Friedel pairs [please check]
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.12 (3)
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
Cr10.00000.00000.03180 (7)0.00963 (13)
C10.07085 (12)0.12933 (16)0.09836 (15)0.0116 (3)
C20.12818 (17)0.05848 (12)0.10119 (14)0.0120 (3)
C30.32426 (11)0.23496 (10)0.10977 (10)0.0166 (2)
H3A0.29900.26530.16700.025*
H3B0.31530.27150.04810.025*
H3C0.40960.25680.11800.025*
C40.08832 (15)0.13608 (15)0.11035 (11)0.0147 (2)
O20.14375 (11)0.22219 (10)0.15796 (8)0.0218 (2)
O10.24923 (10)0.10457 (10)0.10416 (8)0.0145 (2)
H10.1199 (19)0.217 (3)0.091 (2)0.015 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cr10.00922 (15)0.00922 (15)0.01047 (19)0.00461 (7)0.0000.000
C10.0117 (6)0.0101 (7)0.0129 (7)0.0053 (4)0.0013 (4)0.0024 (6)
C20.0104 (7)0.0122 (6)0.0123 (7)0.0049 (4)0.0008 (5)0.0001 (4)
C30.0116 (5)0.0118 (5)0.0224 (5)0.0028 (5)0.0003 (4)0.0014 (4)
C40.0137 (6)0.0153 (6)0.0152 (5)0.0074 (6)0.0008 (5)0.0006 (4)
O20.0191 (5)0.0193 (5)0.0226 (5)0.0062 (5)0.0038 (4)0.0079 (4)
O10.0086 (4)0.0127 (4)0.0202 (5)0.0038 (4)0.0020 (3)0.0010 (4)
Geometric parameters (Å, º) top
Cr1—C41.8459 (17)C1—C2i1.4231 (18)
Cr1—C4i1.8459 (17)C1—H10.97 (3)
Cr1—C4ii1.8459 (17)C2—O11.343 (2)
Cr1—C12.2491 (18)C2—C1ii1.4231 (18)
Cr1—C1ii2.2491 (18)C3—O11.4402 (15)
Cr1—C1i2.2491 (18)C3—H3A0.9800
Cr1—C22.2705 (18)C3—H3B0.9800
Cr1—C2i2.2705 (18)C3—H3C0.9800
Cr1—C2ii2.2705 (18)C4—O21.1515 (19)
C1—C21.4118 (18)
C4—Cr1—C4i90.78 (8)C4—Cr1—C2ii86.51 (7)
C4—Cr1—C4ii90.78 (8)C4i—Cr1—C2ii130.30 (6)
C4i—Cr1—C4ii90.78 (8)C4ii—Cr1—C2ii138.82 (6)
C4—Cr1—C1163.27 (7)C1—Cr1—C2ii77.66 (7)
C4i—Cr1—C1103.55 (7)C1ii—Cr1—C2ii36.40 (4)
C4ii—Cr1—C197.51 (7)C1i—Cr1—C2ii36.70 (4)
C4—Cr1—C1ii103.55 (7)C2—Cr1—C2ii65.09 (8)
C4i—Cr1—C1ii97.51 (7)C2i—Cr1—C2ii65.09 (8)
C4ii—Cr1—C1ii163.27 (7)C2—C1—C2i119.03 (17)
C1—Cr1—C1ii66.47 (8)C2—C1—Cr172.63 (10)
C4—Cr1—C1i97.51 (7)C2i—C1—Cr172.47 (10)
C4i—Cr1—C1i163.27 (7)C2—C1—H1119.4 (12)
C4ii—Cr1—C1i103.55 (7)C2i—C1—H1121.5 (12)
C1—Cr1—C1i66.47 (8)Cr1—C1—H1123.2 (17)
C1ii—Cr1—C1i66.47 (8)O1—C2—C1124.38 (13)
C4—Cr1—C2138.82 (6)O1—C2—C1ii114.77 (12)
C4i—Cr1—C286.51 (7)C1—C2—C1ii120.83 (17)
C4ii—Cr1—C2130.30 (6)O1—C2—Cr1129.93 (13)
C1—Cr1—C236.40 (4)C1—C2—Cr170.98 (10)
C1ii—Cr1—C236.70 (4)C1ii—C2—Cr170.83 (10)
C1i—Cr1—C277.66 (7)O1—C3—H3A109.5
C4—Cr1—C2i130.30 (6)O1—C3—H3B109.5
C4i—Cr1—C2i138.82 (6)H3A—C3—H3B109.5
C4ii—Cr1—C2i86.51 (7)O1—C3—H3C109.5
C1—Cr1—C2i36.70 (4)H3A—C3—H3C109.5
C1ii—Cr1—C2i77.66 (7)H3B—C3—H3C109.5
C1i—Cr1—C2i36.40 (4)O2—C4—Cr1178.85 (15)
C2—Cr1—C2i65.09 (8)C2—O1—C3117.19 (11)
C4—Cr1—C1—C283.9 (2)C1—Cr1—C2—O1119.36 (16)
C4i—Cr1—C1—C264.39 (11)C1ii—Cr1—C2—O1106.71 (14)
C4ii—Cr1—C1—C2157.02 (11)C1i—Cr1—C2—O1173.73 (12)
C1ii—Cr1—C1—C228.00 (11)C2i—Cr1—C2—O1150.07 (13)
C1i—Cr1—C1—C2101.42 (9)C2ii—Cr1—C2—O1137.17 (14)
C2i—Cr1—C1—C2129.20 (19)C4—Cr1—C2—C1154.23 (11)
C2ii—Cr1—C1—C264.54 (9)C4i—Cr1—C2—C1118.56 (11)
C4—Cr1—C1—C2i45.3 (2)C4ii—Cr1—C2—C130.49 (15)
C4i—Cr1—C1—C2i166.41 (11)C1ii—Cr1—C2—C1133.94 (18)
C4ii—Cr1—C1—C2i73.78 (11)C1i—Cr1—C2—C166.92 (9)
C1ii—Cr1—C1—C2i101.20 (8)C2i—Cr1—C2—C130.71 (11)
C1i—Cr1—C1—C2i27.78 (10)C2ii—Cr1—C2—C1103.47 (8)
C2—Cr1—C1—C2i129.20 (19)C4—Cr1—C2—C1ii20.30 (17)
C2ii—Cr1—C1—C2i64.66 (10)C4i—Cr1—C2—C1ii107.50 (11)
C2i—C1—C2—O1176.40 (11)C4ii—Cr1—C2—C1ii164.43 (10)
Cr1—C1—C2—O1125.92 (18)C1—Cr1—C2—C1ii133.94 (18)
C2i—C1—C2—C1ii5.3 (4)C1i—Cr1—C2—C1ii67.02 (9)
Cr1—C1—C2—C1ii52.4 (2)C2i—Cr1—C2—C1ii103.23 (9)
C2i—C1—C2—Cr157.68 (19)C2ii—Cr1—C2—C1ii30.47 (11)
C4—Cr1—C2—O186.41 (16)C1—C2—O1—C33.2 (2)
C4i—Cr1—C2—O10.79 (12)C1ii—C2—O1—C3178.41 (14)
C4ii—Cr1—C2—O188.86 (13)Cr1—C2—O1—C396.49 (12)
Symmetry codes: (i) y, xy, z; (ii) x+y, x, z.
 

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