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The title compound, C13H14O7, is derived from methyl gallate, a protective biological anti­oxidant. It crystallizes with two independent mol­ecules in the asymmetric unit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604918X/gh2012sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680604918X/gh2012Isup2.hkl
Contains datablock I

CCDC reference: 629682

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.073
  • wR factor = 0.208
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B RINTA01_ALERT_3_B The value of Rint is greater than 0.15 Rint given 0.164 PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.16
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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

Methyl 3,5-diacetoxy-4-methoxybenzoate top
Crystal data top
C13H14O7F(000) = 1184
Mr = 282.24Dx = 1.356 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2025 reflections
a = 9.0530 (18) Åθ = 2.1–26.1°
b = 25.769 (5) ŵ = 0.11 mm1
c = 11.864 (2) ÅT = 293 K
β = 92.57 (3)°Prism, colorless
V = 2764.9 (10) Å30.30 × 0.20 × 0.15 mm
Z = 8
Data collection top
Bruker APEX area-detector
diffractometer
5146 independent reflections
Radiation source: fine-focus sealed tube2421 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.164
φ and ω scansθmax = 25.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 010
Tmin = 0.967, Tmax = 0.984k = 031
5484 measured reflectionsl = 1414
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)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0788P)2 + 0.5721P]
where P = (Fo2 + 2Fc2)/3
5146 reflections(Δ/σ)max < 0.001
369 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.31 e Å3
Special details top

Experimental. 1H NMR (CDCl3, 500 MHz): 2.34 (s, 6H, OAc), 3.89 (s, 3H, OMe), 3.90 (s, 3H, OMe), 7.72 (s, 2H, Ar—H).

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
O10.0090 (3)0.36143 (12)0.2798 (2)0.0616 (9)
O20.3803 (4)0.22148 (13)0.6106 (3)0.0755 (10)
O30.2876 (5)0.16001 (15)0.4966 (3)0.0900 (12)
O40.0183 (4)0.36172 (14)0.6142 (3)0.0738 (10)
O50.1419 (3)0.38594 (11)0.4855 (2)0.0553 (8)
O60.2028 (4)0.26101 (17)0.2565 (3)0.0901 (12)
O70.0213 (3)0.26668 (12)0.1874 (2)0.0561 (8)
O80.4689 (4)0.52058 (14)0.3311 (3)0.0818 (11)
O90.8467 (4)0.49233 (16)0.1034 (3)0.0927 (12)
O100.8619 (4)0.41409 (15)0.0240 (3)0.0757 (10)
O110.5758 (4)0.41714 (12)0.3166 (3)0.0691 (9)
O120.7807 (4)0.43833 (15)0.4177 (3)0.0812 (11)
O130.4966 (3)0.58549 (13)0.1519 (3)0.0683 (9)
O140.6618 (4)0.62135 (13)0.2725 (3)0.0837 (11)
C10.0733 (5)0.32573 (17)0.3384 (3)0.0469 (10)
C20.1443 (5)0.33548 (16)0.4432 (3)0.0466 (11)
C30.2204 (5)0.29716 (17)0.5013 (3)0.0505 (11)
H30.26830.30460.57040.061*
C40.2263 (5)0.24775 (17)0.4579 (4)0.0502 (11)
C50.1556 (4)0.23694 (17)0.3525 (3)0.0516 (11)
H50.15860.20370.32200.062*
C60.0829 (4)0.27579 (18)0.2961 (3)0.0481 (11)
C70.2997 (5)0.2046 (2)0.5208 (4)0.0575 (12)
C80.0671 (6)0.4054 (2)0.2387 (4)0.0818 (16)
H8A0.13090.41940.29800.123*
H8B0.00330.43120.21370.123*
H8C0.12510.39510.17670.123*
C90.0566 (5)0.39462 (19)0.5763 (4)0.0556 (12)
C100.0735 (5)0.44868 (18)0.6159 (4)0.0665 (14)
H10A0.00970.45800.65910.100*
H10B0.07860.47140.55220.100*
H10C0.16260.45180.66240.100*
C110.1268 (6)0.26246 (19)0.1774 (4)0.0597 (12)
C120.1771 (6)0.2610 (2)0.0561 (4)0.0826 (17)
H12A0.28130.25410.05000.124*
H12B0.12480.23420.01830.124*
H12C0.15740.29390.02170.124*
C130.4499 (6)0.1816 (2)0.6811 (5)0.0917 (18)
H13A0.37540.16270.71880.138*
H13B0.51650.19750.73610.138*
H13C0.50390.15840.63510.138*
C140.5471 (5)0.50390 (19)0.2421 (4)0.0570 (12)
C150.5724 (5)0.53867 (19)0.1554 (4)0.0554 (12)
C160.6586 (5)0.52527 (19)0.0681 (4)0.0555 (12)
H160.67470.54910.01100.067*
C170.7218 (5)0.47634 (18)0.0643 (3)0.0521 (11)
C180.6930 (5)0.44094 (18)0.1483 (4)0.0543 (11)
H180.73160.40750.14510.065*
C190.6082 (5)0.45478 (18)0.2359 (3)0.0526 (11)
C200.8154 (5)0.4627 (2)0.0300 (4)0.0620 (13)
C210.3409 (6)0.4948 (3)0.3568 (5)0.108 (2)
H21A0.33950.46120.32200.162*
H21B0.25670.51450.32930.162*
H21C0.33750.49090.43720.162*
C220.5510 (6)0.6252 (2)0.2171 (4)0.0636 (13)
C230.4531 (6)0.6710 (2)0.2071 (5)0.0883 (17)
H23A0.36680.66520.24950.132*
H23B0.42400.67650.12920.132*
H23C0.50490.70100.23600.132*
C240.6749 (6)0.4123 (2)0.4062 (4)0.0627 (13)
C250.6228 (7)0.3704 (2)0.4825 (5)0.108 (2)
H25A0.61890.33800.44260.162*
H25B0.52600.37890.50680.162*
H25C0.69010.36750.54710.162*
C260.9566 (7)0.3966 (3)0.1115 (5)0.114 (2)
H26A0.90110.39550.18230.171*
H26B0.99360.36260.09320.171*
H26C1.03800.42020.11710.171*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.069 (2)0.058 (2)0.0569 (19)0.0002 (17)0.0145 (16)0.0125 (16)
O20.081 (2)0.064 (2)0.078 (2)0.0072 (18)0.025 (2)0.0105 (19)
O30.138 (3)0.054 (2)0.076 (2)0.018 (2)0.014 (2)0.001 (2)
O40.094 (3)0.060 (2)0.069 (2)0.008 (2)0.022 (2)0.0049 (18)
O50.077 (2)0.0460 (19)0.0426 (17)0.0048 (15)0.0000 (15)0.0019 (14)
O60.066 (2)0.141 (4)0.064 (2)0.030 (2)0.0055 (19)0.001 (2)
O70.060 (2)0.074 (2)0.0335 (16)0.0065 (16)0.0004 (14)0.0118 (14)
O80.080 (2)0.096 (3)0.072 (2)0.022 (2)0.026 (2)0.032 (2)
O90.125 (3)0.093 (3)0.062 (2)0.003 (2)0.026 (2)0.019 (2)
O100.093 (3)0.079 (3)0.056 (2)0.018 (2)0.0205 (18)0.0005 (18)
O110.085 (2)0.067 (2)0.055 (2)0.0207 (18)0.0066 (18)0.0023 (17)
O120.097 (3)0.083 (3)0.062 (2)0.025 (2)0.011 (2)0.0055 (19)
O130.068 (2)0.061 (2)0.074 (2)0.0069 (18)0.0195 (17)0.0085 (18)
O140.100 (3)0.066 (2)0.081 (3)0.006 (2)0.035 (2)0.0123 (19)
C10.050 (3)0.051 (3)0.040 (2)0.004 (2)0.002 (2)0.003 (2)
C20.057 (3)0.047 (3)0.036 (2)0.002 (2)0.002 (2)0.003 (2)
C30.057 (3)0.056 (3)0.039 (2)0.002 (2)0.001 (2)0.003 (2)
C40.052 (3)0.051 (3)0.048 (3)0.000 (2)0.003 (2)0.000 (2)
C50.056 (3)0.048 (3)0.052 (3)0.001 (2)0.008 (2)0.007 (2)
C60.051 (3)0.059 (3)0.034 (2)0.001 (2)0.0017 (19)0.004 (2)
C70.065 (3)0.053 (3)0.055 (3)0.005 (3)0.007 (2)0.006 (3)
C80.090 (4)0.078 (4)0.076 (4)0.014 (3)0.004 (3)0.029 (3)
C90.070 (3)0.054 (3)0.042 (3)0.000 (3)0.008 (2)0.001 (2)
C100.090 (4)0.054 (3)0.054 (3)0.009 (3)0.013 (3)0.007 (2)
C110.056 (3)0.069 (3)0.054 (3)0.010 (3)0.003 (2)0.002 (2)
C120.093 (4)0.099 (4)0.054 (3)0.004 (3)0.018 (3)0.007 (3)
C130.090 (4)0.083 (4)0.099 (4)0.019 (3)0.027 (3)0.030 (3)
C140.058 (3)0.064 (3)0.048 (3)0.015 (3)0.002 (2)0.016 (2)
C150.057 (3)0.052 (3)0.056 (3)0.002 (2)0.013 (2)0.008 (2)
C160.058 (3)0.062 (3)0.045 (3)0.004 (2)0.011 (2)0.004 (2)
C170.055 (3)0.059 (3)0.042 (2)0.002 (2)0.002 (2)0.004 (2)
C180.062 (3)0.049 (3)0.051 (3)0.004 (2)0.001 (2)0.005 (2)
C190.070 (3)0.048 (3)0.040 (2)0.008 (2)0.004 (2)0.003 (2)
C200.070 (3)0.073 (4)0.042 (3)0.001 (3)0.002 (2)0.005 (3)
C210.079 (4)0.150 (6)0.096 (5)0.025 (4)0.034 (4)0.031 (4)
C220.074 (4)0.061 (3)0.055 (3)0.005 (3)0.005 (3)0.004 (3)
C230.110 (5)0.068 (4)0.086 (4)0.023 (3)0.002 (3)0.003 (3)
C240.084 (4)0.059 (3)0.044 (3)0.007 (3)0.002 (3)0.005 (2)
C250.132 (5)0.107 (5)0.084 (4)0.031 (4)0.006 (4)0.048 (4)
C260.140 (6)0.109 (5)0.097 (5)0.031 (4)0.061 (4)0.002 (4)
Geometric parameters (Å, º) top
O1—C11.356 (5)C9—C101.476 (6)
O1—C81.423 (5)C10—H10A0.9600
O2—C71.337 (5)C10—H10B0.9600
O2—C131.450 (5)C10—H10C0.9600
O3—C71.188 (5)C11—C121.491 (6)
O4—C91.187 (5)C12—H12A0.9600
O5—C91.371 (5)C12—H12B0.9600
O5—C21.394 (5)C12—H12C0.9600
O6—C111.189 (5)C13—H13A0.9600
O7—C111.345 (5)C13—H13B0.9600
O7—C61.401 (5)C13—H13C0.9600
O8—C141.366 (5)C14—C191.385 (6)
O8—C211.382 (6)C14—C151.391 (6)
O9—C201.201 (5)C15—C161.369 (6)
O10—C201.323 (6)C16—C171.386 (6)
O10—C261.448 (6)C16—H160.9300
O11—C241.366 (6)C17—C181.384 (6)
O11—C191.403 (5)C17—C201.476 (6)
O12—C241.173 (5)C18—C191.367 (6)
O13—C221.361 (6)C18—H180.9300
O13—C151.388 (5)C21—H21A0.9600
O14—C221.178 (5)C21—H21B0.9600
C1—C61.386 (6)C21—H21C0.9600
C1—C21.397 (5)C22—C231.477 (7)
C2—C31.372 (6)C23—H23A0.9600
C3—C41.375 (6)C23—H23B0.9600
C3—H30.9300C23—H23C0.9600
C4—C51.407 (6)C24—C251.498 (7)
C4—C71.480 (6)C25—H25A0.9600
C5—C61.358 (6)C25—H25B0.9600
C5—H50.9300C25—H25C0.9600
C8—H8A0.9600C26—H26A0.9600
C8—H8B0.9600C26—H26B0.9600
C8—H8C0.9600C26—H26C0.9600
C1—O1—C8116.9 (4)H13A—C13—H13B109.5
C7—O2—C13115.9 (4)O2—C13—H13C109.5
C9—O5—C2116.9 (3)H13A—C13—H13C109.5
C11—O7—C6116.7 (3)H13B—C13—H13C109.5
C14—O8—C21119.2 (4)O8—C14—C19123.4 (4)
C20—O10—C26116.9 (4)O8—C14—C15118.5 (5)
C24—O11—C19116.4 (4)C19—C14—C15118.0 (4)
C22—O13—C15118.1 (4)C16—C15—O13119.7 (4)
O1—C1—C6119.1 (4)C16—C15—C14121.1 (5)
O1—C1—C2123.7 (4)O13—C15—C14118.9 (4)
C6—C1—C2117.1 (4)C15—C16—C17120.3 (4)
C3—C2—O5120.4 (4)C15—C16—H16119.9
C3—C2—C1121.2 (4)C17—C16—H16119.9
O5—C2—C1118.3 (4)C18—C17—C16119.0 (4)
C2—C3—C4120.4 (4)C18—C17—C20121.5 (4)
C2—C3—H3119.8C16—C17—C20119.5 (4)
C4—C3—H3119.8C19—C18—C17120.4 (4)
C3—C4—C5119.5 (4)C19—C18—H18119.8
C3—C4—C7122.1 (4)C17—C18—H18119.8
C5—C4—C7118.4 (4)C18—C19—C14121.2 (4)
C6—C5—C4118.9 (4)C18—C19—O11118.7 (4)
C6—C5—H5120.5C14—C19—O11120.0 (4)
C4—C5—H5120.5O9—C20—O10123.8 (5)
C5—C6—C1122.9 (4)O9—C20—C17124.1 (5)
C5—C6—O7119.6 (4)O10—C20—C17112.1 (4)
C1—C6—O7117.4 (4)O8—C21—H21A109.5
O3—C7—O2123.3 (4)O8—C21—H21B109.5
O3—C7—C4124.7 (5)H21A—C21—H21B109.5
O2—C7—C4112.0 (4)O8—C21—H21C109.5
O1—C8—H8A109.5H21A—C21—H21C109.5
O1—C8—H8B109.5H21B—C21—H21C109.5
H8A—C8—H8B109.5O14—C22—O13122.1 (5)
O1—C8—H8C109.5O14—C22—C23127.2 (5)
H8A—C8—H8C109.5O13—C22—C23110.8 (5)
H8B—C8—H8C109.5C22—C23—H23A109.5
O4—C9—O5122.2 (4)C22—C23—H23B109.5
O4—C9—C10127.3 (5)H23A—C23—H23B109.5
O5—C9—C10110.5 (4)C22—C23—H23C109.5
C9—C10—H10A109.5H23A—C23—H23C109.5
C9—C10—H10B109.5H23B—C23—H23C109.5
H10A—C10—H10B109.5O12—C24—O11122.8 (5)
C9—C10—H10C109.5O12—C24—C25128.3 (5)
H10A—C10—H10C109.5O11—C24—C25108.9 (5)
H10B—C10—H10C109.5C24—C25—H25A109.5
O6—C11—O7122.9 (4)C24—C25—H25B109.5
O6—C11—C12126.8 (5)H25A—C25—H25B109.5
O7—C11—C12110.3 (4)C24—C25—H25C109.5
C11—C12—H12A109.5H25A—C25—H25C109.5
C11—C12—H12B109.5H25B—C25—H25C109.5
H12A—C12—H12B109.5O10—C26—H26A109.5
C11—C12—H12C109.5O10—C26—H26B109.5
H12A—C12—H12C109.5H26A—C26—H26B109.5
H12B—C12—H12C109.5O10—C26—H26C109.5
O2—C13—H13A109.5H26A—C26—H26C109.5
O2—C13—H13B109.5H26B—C26—H26C109.5
C8—O1—C1—C6117.2 (5)C21—O8—C14—C1960.9 (6)
C8—O1—C1—C266.2 (6)C21—O8—C14—C15122.1 (5)
C9—O5—C2—C373.6 (5)C22—O13—C15—C16103.8 (5)
C9—O5—C2—C1109.4 (4)C22—O13—C15—C1482.9 (5)
O1—C1—C2—C3176.9 (4)O8—C14—C15—C16175.4 (4)
C6—C1—C2—C30.2 (6)C19—C14—C15—C161.8 (6)
O1—C1—C2—O56.1 (6)O8—C14—C15—O1311.3 (6)
C6—C1—C2—O5177.2 (4)C19—C14—C15—O13171.5 (4)
O5—C2—C3—C4178.1 (4)O13—C15—C16—C17172.9 (4)
C1—C2—C3—C41.1 (6)C14—C15—C16—C170.3 (6)
C2—C3—C4—C51.0 (6)C15—C16—C17—C181.9 (6)
C2—C3—C4—C7176.3 (4)C15—C16—C17—C20179.5 (4)
C3—C4—C5—C60.0 (6)C16—C17—C18—C192.6 (6)
C7—C4—C5—C6177.4 (4)C20—C17—C18—C19178.8 (4)
C4—C5—C6—C10.9 (6)C17—C18—C19—C141.1 (6)
C4—C5—C6—O7175.3 (4)C17—C18—C19—O11177.1 (4)
O1—C1—C6—C5176.0 (4)O8—C14—C19—C18176.0 (4)
C2—C1—C6—C50.8 (6)C15—C14—C19—C181.1 (6)
O1—C1—C6—O77.7 (6)O8—C14—C19—O118.1 (6)
C2—C1—C6—O7175.4 (4)C15—C14—C19—O11174.9 (4)
C11—O7—C6—C5106.6 (5)C24—O11—C19—C1888.7 (5)
C11—O7—C6—C177.0 (5)C24—O11—C19—C1495.2 (5)
C13—O2—C7—O32.2 (7)C26—O10—C20—O90.4 (7)
C13—O2—C7—C4176.7 (4)C26—O10—C20—C17179.1 (4)
C3—C4—C7—O3167.0 (5)C18—C17—C20—O9178.1 (5)
C5—C4—C7—O310.3 (7)C16—C17—C20—O93.3 (7)
C3—C4—C7—O211.9 (6)C18—C17—C20—O101.4 (6)
C5—C4—C7—O2170.8 (4)C16—C17—C20—O10177.2 (4)
C2—O5—C9—O43.8 (6)C15—O13—C22—O142.5 (7)
C2—O5—C9—C10176.1 (3)C15—O13—C22—C23177.3 (4)
C6—O7—C11—O67.6 (7)C19—O11—C24—O121.3 (7)
C6—O7—C11—C12171.3 (4)C19—O11—C24—C25179.7 (4)
 

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