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In the title compound, C18H20O2, the C(=O)O group is twisted by 68.1 (1)° from the plane of the 2,3,4,6-tetra­methyl­benzyl ring. The methyl­ene C atom is almost coplanar with the carbonylate group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806000535/bt6797sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806000535/bt6797Isup2.hkl
Contains datablock I

CCDC reference: 298372

Key indicators

  • Single-crystal X-ray study
  • T = 110 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.044
  • wR factor = 0.123
  • Data-to-parameter ratio = 19.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

Benzyl 2,3,4,6-tetramethylbenzoate top
Crystal data top
C18H20O2F(000) = 576
Mr = 268.34Dx = 1.209 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 15.4921 (19) ÅCell parameters from 4540 reflections
b = 5.5915 (8) Åθ = 2.7–28.3°
c = 17.1846 (19) ŵ = 0.08 mm1
β = 97.815 (5)°T = 110 K
V = 1474.8 (3) Å3Plate, colorless
Z = 40.13 × 0.12 × 0.11 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3631 independent reflections
Radiation source: fine-focus sealed tube3026 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2017
Tmin = 0.984, Tmax = 0.993k = 67
11515 measured reflectionsl = 1222
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0578P)2 + 0.5741P]
where P = (Fo2 + 2Fc2)/3
3631 reflections(Δ/σ)max = 0.001
185 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.21 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
O10.09279 (6)0.31042 (19)1.00871 (5)0.0268 (2)
O20.06266 (5)0.19852 (17)0.88197 (5)0.0214 (2)
C10.20844 (8)0.2896 (2)0.92897 (6)0.0182 (2)
C20.23217 (8)0.4661 (2)0.87782 (6)0.0206 (3)
C30.31966 (9)0.4800 (2)0.86375 (7)0.0232 (3)
C40.38123 (9)0.3203 (3)0.90165 (7)0.0253 (3)
C50.35490 (8)0.1466 (3)0.95163 (7)0.0240 (3)
H50.39620.04020.97600.029*
C60.26911 (8)0.1264 (2)0.96644 (6)0.0196 (3)
C70.11626 (8)0.2709 (2)0.94551 (7)0.0193 (3)
C80.02957 (8)0.1789 (3)0.89148 (7)0.0236 (3)
H8A0.04900.32360.91500.028*
H8B0.03860.04480.92520.028*
C90.07959 (8)0.1422 (2)0.81099 (7)0.0197 (3)
C100.13104 (8)0.0597 (2)0.79414 (7)0.0214 (3)
H100.13290.17680.83230.026*
C110.17982 (8)0.0878 (2)0.72027 (7)0.0227 (3)
H110.21490.22210.70960.027*
C120.17609 (8)0.0842 (2)0.66274 (7)0.0227 (3)
H120.20870.06580.61350.027*
C130.12343 (8)0.2842 (2)0.67896 (7)0.0235 (3)
H130.12010.39850.64020.028*
C140.07584 (8)0.3141 (2)0.75273 (7)0.0225 (3)
H140.04130.44940.76340.027*
C150.16575 (9)0.6417 (3)0.83902 (7)0.0262 (3)
H15A0.15310.60560.78400.039*
H15B0.18860.80110.84560.039*
H15C0.11330.63010.86280.039*
C160.34597 (11)0.6657 (3)0.80748 (8)0.0330 (3)
H16A0.35160.81850.83310.049*
H16B0.30230.67500.76230.049*
H16C0.40070.62140.79130.049*
C170.47588 (10)0.3308 (3)0.88907 (9)0.0392 (4)
H17A0.50740.20400.91790.059*
H17B0.50020.48200.90720.059*
H17C0.48010.31300.83420.059*
C180.24279 (9)0.0687 (2)1.01944 (7)0.0239 (3)
H18A0.28830.18611.02800.036*
H18B0.19010.14330.99510.036*
H18C0.23320.00071.06890.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0267 (5)0.0360 (6)0.0178 (4)0.0019 (4)0.0034 (3)0.0033 (4)
O20.0175 (4)0.0283 (5)0.0184 (4)0.0007 (4)0.0018 (3)0.0036 (3)
C10.0204 (6)0.0191 (6)0.0147 (5)0.0007 (5)0.0007 (4)0.0029 (4)
C20.0281 (7)0.0177 (6)0.0157 (5)0.0021 (5)0.0015 (4)0.0026 (4)
C30.0306 (7)0.0213 (6)0.0182 (5)0.0053 (5)0.0054 (5)0.0029 (5)
C40.0242 (7)0.0298 (7)0.0223 (6)0.0031 (5)0.0045 (5)0.0033 (5)
C50.0230 (6)0.0275 (7)0.0209 (5)0.0032 (5)0.0009 (5)0.0005 (5)
C60.0224 (6)0.0205 (6)0.0154 (5)0.0013 (5)0.0002 (4)0.0021 (4)
C70.0222 (6)0.0176 (6)0.0176 (5)0.0016 (5)0.0011 (4)0.0006 (4)
C80.0176 (6)0.0332 (7)0.0205 (5)0.0010 (5)0.0037 (4)0.0008 (5)
C90.0159 (6)0.0234 (6)0.0198 (5)0.0027 (5)0.0027 (4)0.0015 (5)
C100.0207 (6)0.0222 (6)0.0221 (5)0.0023 (5)0.0058 (4)0.0026 (5)
C110.0210 (6)0.0207 (6)0.0266 (6)0.0012 (5)0.0040 (5)0.0042 (5)
C120.0212 (6)0.0259 (7)0.0205 (5)0.0029 (5)0.0009 (4)0.0031 (5)
C130.0238 (6)0.0230 (7)0.0234 (6)0.0033 (5)0.0022 (5)0.0046 (5)
C140.0198 (6)0.0212 (6)0.0262 (6)0.0002 (5)0.0017 (5)0.0003 (5)
C150.0348 (7)0.0208 (6)0.0219 (6)0.0017 (5)0.0004 (5)0.0016 (5)
C160.0432 (9)0.0297 (8)0.0279 (6)0.0063 (6)0.0113 (6)0.0024 (6)
C170.0272 (8)0.0520 (10)0.0399 (8)0.0016 (7)0.0105 (6)0.0054 (7)
C180.0265 (7)0.0242 (7)0.0205 (5)0.0006 (5)0.0015 (5)0.0031 (5)
Geometric parameters (Å, º) top
O1—C71.2116 (14)C10—H100.9300
O2—C71.3412 (14)C11—C121.3860 (18)
O2—C81.4642 (15)C11—H110.9300
C1—C61.4024 (17)C12—C131.3902 (19)
C1—C21.4031 (17)C12—H120.9300
C1—C71.4973 (17)C13—C141.3871 (17)
C2—C31.4109 (18)C13—H130.9300
C2—C151.5103 (18)C14—H140.9300
C3—C41.4007 (19)C15—H15A0.9600
C3—C161.5121 (18)C15—H15B0.9600
C4—C51.3942 (19)C15—H15C0.9600
C4—C171.5120 (19)C16—H16A0.9600
C5—C61.3914 (17)C16—H16B0.9600
C5—H50.9300C16—H16C0.9600
C6—C181.5124 (17)C17—H17A0.9600
C8—C91.5048 (17)C17—H17B0.9600
C8—H8A0.9700C17—H17C0.9600
C8—H8B0.9700C18—H18A0.9600
C9—C101.3899 (18)C18—H18B0.9600
C9—C141.3948 (17)C18—H18C0.9600
C10—C111.3951 (17)
C7—O2—C8115.92 (9)C12—C11—H11120.0
C6—C1—C2121.94 (11)C10—C11—H11120.0
C6—C1—C7117.65 (11)C11—C12—C13119.70 (12)
C2—C1—C7120.41 (11)C11—C12—H12120.2
C1—C2—C3119.05 (11)C13—C12—H12120.2
C1—C2—C15120.86 (11)C14—C13—C12120.32 (12)
C3—C2—C15120.08 (11)C14—C13—H13119.8
C4—C3—C2119.64 (11)C12—C13—H13119.8
C4—C3—C16120.61 (12)C13—C14—C9120.26 (12)
C2—C3—C16119.75 (12)C13—C14—H14119.9
C5—C4—C3119.52 (12)C9—C14—H14119.9
C5—C4—C17119.06 (13)C2—C15—H15A109.5
C3—C4—C17121.42 (13)C2—C15—H15B109.5
C6—C5—C4122.41 (12)H15A—C15—H15B109.5
C6—C5—H5118.8C2—C15—H15C109.5
C4—C5—H5118.8H15A—C15—H15C109.5
C5—C6—C1117.42 (11)H15B—C15—H15C109.5
C5—C6—C18120.73 (11)C3—C16—H16A109.5
C1—C6—C18121.83 (11)C3—C16—H16B109.5
O1—C7—O2123.84 (11)H16A—C16—H16B109.5
O1—C7—C1124.58 (11)C3—C16—H16C109.5
O2—C7—C1111.56 (9)H16A—C16—H16C109.5
O2—C8—C9107.21 (9)H16B—C16—H16C109.5
O2—C8—H8A110.3C4—C17—H17A109.5
C9—C8—H8A110.3C4—C17—H17B109.5
O2—C8—H8B110.3H17A—C17—H17B109.5
C9—C8—H8B110.3C4—C17—H17C109.5
H8A—C8—H8B108.5H17A—C17—H17C109.5
C10—C9—C14119.28 (11)H17B—C17—H17C109.5
C10—C9—C8120.75 (11)C6—C18—H18A109.5
C14—C9—C8119.96 (12)C6—C18—H18B109.5
C9—C10—C11120.35 (12)H18A—C18—H18B109.5
C9—C10—H10119.8C6—C18—H18C109.5
C11—C10—H10119.8H18A—C18—H18C109.5
C12—C11—C10120.07 (12)H18B—C18—H18C109.5
C2—C1—C7—O268.18 (15)C1—C7—O2—C8178.81 (10)
 

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