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The title compound, C13H11NO6, a modified aspirin, was characterized by 1H NMR, solid-state IR and X-ray crystallographic techniques. The X-ray structure determination reveals that the twist of the acetyl group with respect to the phenyl ring is 12° less than that in aspirin. Also, the carboxyl plane is twisted out of the plane of the phenyl ring, probably due to the succin­imide substitution. The crystal structure is stabilized by C—H...O and π–π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022237/ci6183sup1.cif
Contains datablocks global, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022237/ci61833sup2.hkl
Contains datablock 3

CCDC reference: 203013

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.069
  • wR factor = 0.187
  • Data-to-parameter ratio = 12.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Succinimido 2-acetoxybenzoate top
Crystal data top
C13H11NO6F(000) = 576
Mr = 277.23Dx = 1.442 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 438 reflections
a = 5.930 (3) Åθ = 2.3–22.5°
b = 9.647 (6) ŵ = 0.12 mm1
c = 22.331 (9) ÅT = 293 K
β = 90.64 (5)°Plate, colorless
V = 1277.4 (11) Å30.30 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker CCD area-detector
diffractometer
2352 independent reflections
Radiation source: fine-focus sealed tube1428 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.084
φ and ω scansθmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 76
Tmin = 0.925, Tmax = 1.000k = 811
5185 measured reflectionsl = 2426
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)] = 0.069H-atom parameters constrained
wR(F2) = 0.187 w = 1/[σ2(Fo2) + (0.0509P)2 + 1.2437P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.001
2352 reflectionsΔρmax = 0.22 e Å3
183 parametersΔρmin = 0.41 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.052 (5)
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
N10.0941 (5)0.0810 (4)0.18393 (14)0.0518 (9)
O10.1122 (6)0.2980 (3)0.22042 (15)0.0756 (10)
O20.0027 (6)0.1385 (4)0.15973 (15)0.0854 (11)
O30.1812 (4)0.1152 (3)0.12741 (11)0.0575 (8)
O40.5246 (5)0.0962 (4)0.16843 (12)0.0749 (10)
O50.1794 (4)0.3149 (3)0.04471 (12)0.0513 (7)
O60.3693 (6)0.4527 (3)0.10617 (14)0.0672 (9)
C10.0564 (7)0.1812 (5)0.22595 (18)0.0541 (10)
C20.0632 (8)0.1107 (4)0.27604 (18)0.0622 (12)
H2A0.20660.15550.28360.075*
H2B0.02740.11330.31250.075*
C30.0985 (7)0.0355 (4)0.25577 (17)0.0572 (11)
H3A0.25810.05750.25430.069*
H3B0.02390.09950.28300.069*
C40.0029 (7)0.0454 (5)0.19346 (19)0.0534 (11)
C50.4124 (6)0.1221 (4)0.12646 (16)0.0458 (9)
C60.4904 (6)0.1611 (4)0.06587 (15)0.0398 (9)
C70.6890 (6)0.1026 (4)0.04634 (17)0.0467 (9)
H70.76910.04330.07160.056*
C80.7709 (7)0.1308 (4)0.01013 (18)0.0529 (11)
H80.90450.09010.02270.063*
C90.6569 (8)0.2172 (4)0.0468 (2)0.0610 (12)
H90.71040.23520.08500.073*
C100.4612 (7)0.2788 (4)0.02782 (19)0.0585 (11)
H100.38390.33970.05300.070*
C110.3794 (6)0.2507 (4)0.02833 (16)0.0421 (9)
C120.1955 (8)0.4177 (4)0.08515 (19)0.0520 (10)
C130.0314 (8)0.4751 (5)0.0983 (2)0.0850 (16)
H13A0.12550.40300.11390.127*
H13B0.09800.51120.06220.127*
H13C0.01710.54810.12730.127*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.047 (2)0.066 (2)0.0427 (18)0.0024 (17)0.0066 (15)0.0049 (16)
O10.075 (2)0.064 (2)0.088 (2)0.0090 (17)0.0150 (18)0.0042 (17)
O20.094 (3)0.073 (2)0.090 (2)0.0109 (19)0.025 (2)0.022 (2)
O30.0391 (16)0.087 (2)0.0464 (15)0.0048 (14)0.0018 (12)0.0108 (14)
O40.0489 (18)0.121 (3)0.0551 (18)0.0161 (18)0.0026 (15)0.0224 (18)
O50.0348 (15)0.0558 (16)0.0634 (17)0.0106 (12)0.0031 (13)0.0020 (14)
O60.066 (2)0.0568 (18)0.079 (2)0.0026 (15)0.0019 (17)0.0149 (15)
C10.048 (2)0.058 (3)0.057 (2)0.000 (2)0.003 (2)0.007 (2)
C20.066 (3)0.069 (3)0.052 (2)0.007 (2)0.016 (2)0.006 (2)
C30.057 (3)0.062 (3)0.054 (2)0.007 (2)0.008 (2)0.013 (2)
C40.044 (2)0.062 (3)0.055 (3)0.003 (2)0.014 (2)0.005 (2)
C50.036 (2)0.055 (2)0.046 (2)0.0042 (17)0.0004 (17)0.0014 (18)
C60.032 (2)0.0412 (19)0.046 (2)0.0003 (16)0.0009 (16)0.0038 (16)
C70.040 (2)0.044 (2)0.056 (2)0.0052 (17)0.0012 (18)0.0021 (18)
C80.044 (2)0.050 (2)0.065 (3)0.0062 (18)0.018 (2)0.002 (2)
C90.062 (3)0.058 (3)0.063 (3)0.008 (2)0.015 (2)0.013 (2)
C100.058 (3)0.052 (2)0.066 (3)0.015 (2)0.002 (2)0.016 (2)
C110.036 (2)0.041 (2)0.049 (2)0.0029 (17)0.0055 (17)0.0006 (17)
C120.053 (3)0.041 (2)0.062 (3)0.0136 (19)0.009 (2)0.0064 (19)
C130.072 (4)0.089 (4)0.094 (4)0.045 (3)0.011 (3)0.002 (3)
Geometric parameters (Å, º) top
N1—C41.352 (5)C3—H3B0.97
N1—C11.367 (5)C5—C61.483 (5)
N1—O31.408 (4)C6—C111.368 (5)
O1—C11.181 (5)C6—C71.381 (5)
O2—C41.172 (5)C7—C81.383 (5)
O3—C51.373 (4)C7—H70.93
O4—C51.170 (4)C8—C91.346 (6)
O5—C121.344 (5)C8—H80.93
O5—C111.391 (4)C9—C101.375 (6)
O6—C121.177 (5)C9—H90.93
C1—C21.495 (6)C10—C111.377 (5)
C2—C31.495 (6)C10—H100.93
C2—H2A0.97C12—C131.487 (6)
C2—H2B0.97C13—H13A0.96
C3—C41.525 (5)C13—H13B0.96
C3—H3A0.97C13—H13C0.96
C4—N1—C1117.5 (3)C11—C6—C5124.5 (3)
C4—N1—O3120.3 (3)C7—C6—C5117.4 (3)
C1—N1—O3120.9 (3)C6—C7—C8121.2 (4)
C5—O3—N1113.7 (3)C6—C7—H7119.4
C12—O5—C11116.8 (3)C8—C7—H7119.4
O1—C1—N1123.7 (4)C9—C8—C7119.8 (4)
O1—C1—C2130.4 (4)C9—C8—H8120.1
N1—C1—C2105.9 (4)C7—C8—H8120.1
C1—C2—C3105.6 (3)C8—C9—C10120.0 (4)
C1—C2—H2A110.6C8—C9—H9120.0
C3—C2—H2A110.6C10—C9—H9120.0
C1—C2—H2B110.6C9—C10—C11120.2 (4)
C3—C2—H2B110.6C9—C10—H10119.9
H2A—C2—H2B108.8C11—C10—H10119.9
C2—C3—C4106.3 (3)C6—C11—C10120.7 (3)
C2—C3—H3A110.5C6—C11—O5121.8 (3)
C4—C3—H3A110.5C10—C11—O5117.5 (3)
C2—C3—H3B110.5O6—C12—O5122.3 (4)
C4—C3—H3B110.5O6—C12—C13127.2 (4)
H3A—C3—H3B108.7O5—C12—C13110.5 (4)
O2—C4—N1126.0 (4)C12—C13—H13A109.5
O2—C4—C3129.6 (4)C12—C13—H13B109.5
N1—C4—C3104.4 (4)H13A—C13—H13B109.5
O4—C5—O3122.4 (4)C12—C13—H13C109.5
O4—C5—C6127.2 (4)H13A—C13—H13C109.5
O3—C5—C6110.4 (3)H13B—C13—H13C109.5
C11—C6—C7118.1 (3)
C4—N1—O3—C5108.0 (4)O3—C5—C6—C1135.2 (5)
C1—N1—O3—C585.7 (4)O4—C5—C6—C733.2 (6)
C4—N1—C1—O1174.0 (4)O3—C5—C6—C7144.9 (3)
O3—N1—C1—O17.3 (6)C11—C6—C7—C81.7 (5)
C4—N1—C1—C25.9 (5)C5—C6—C7—C8178.4 (3)
O3—N1—C1—C2172.6 (3)C6—C7—C8—C90.4 (6)
O1—C1—C2—C3176.8 (5)C7—C8—C9—C100.9 (6)
N1—C1—C2—C33.1 (5)C8—C9—C10—C111.1 (7)
C1—C2—C3—C40.1 (5)C7—C6—C11—C101.5 (5)
C1—N1—C4—O2173.1 (4)C5—C6—C11—C10178.5 (3)
O3—N1—C4—O26.3 (6)C7—C6—C11—O5179.4 (3)
C1—N1—C4—C35.9 (5)C5—C6—C11—O50.5 (6)
O3—N1—C4—C3172.7 (3)C9—C10—C11—C60.2 (6)
C2—C3—C4—O2175.6 (5)C9—C10—C11—O5179.3 (4)
C2—C3—C4—N13.3 (4)C12—O5—C11—C673.7 (4)
N1—O3—C5—O42.9 (6)C12—O5—C11—C10107.3 (4)
N1—O3—C5—C6178.9 (3)C11—O5—C12—O60.1 (5)
O4—C5—C6—C11146.7 (5)C11—O5—C12—C13179.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···O2i0.932.573.335 (6)140
C2—H2B···O6ii0.972.463.240 (6)137
C3—H3A···O1iii0.972.593.490 (6)155
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y1/2, z+1/2; (iii) x1/2, y1/2, z+1/2.
 

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