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The asymmetric unit of the title compound, C22H14O6·2C2H4O2, contains one half-mol­ecule of 2,5-dibenzoyl­terephthalic acid (DBTA) and one acetic acid mol­ecule. The DBTA mol­ecule is centrosymmetric. The acetic acid mol­ecules are linked to DBTA by strong O—H...O hydrogen bonds, which may be effective in the stabilization of the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038827/hk2134sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038827/hk2134Isup2.hkl
Contains datablock I

CCDC reference: 624732

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.057
  • wR factor = 0.169
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C13
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

2,5-Dibenzoylterephthalic acid acetic acid disolvate top
Crystal data top
C22H14O6·2C2H4O2Z = 1
Mr = 494.44F(000) = 258
Triclinic, P1Dx = 1.344 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.6380 (11) ÅCell parameters from 25 reflections
b = 9.889 (2) Åθ = 9–12°
c = 11.387 (2) ŵ = 0.10 mm1
α = 79.60 (3)°T = 298 K
β = 78.92 (3)°Block, colourless
γ = 83.76 (3)°0.40 × 0.20 × 0.20 mm
V = 611.0 (2) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
1453 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 26.0°, θmin = 1.9°
ω/2θ scansh = 66
Absorption correction: ψ scan
(North et al., 1968)
k = 1112
Tmin = 0.959, Tmax = 0.979l = 014
2388 measured reflections3 standard reflections every 120 min
2388 independent reflections intensity decay: none
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.09P)2]
where P = (Fo2 + 2Fc2)/3
2388 reflections(Δ/σ)max < 0.001
164 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.18 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
O10.4308 (4)0.7611 (2)0.46037 (19)0.0714 (6)
O20.2457 (3)0.34137 (19)0.76825 (16)0.0561 (5)
H2B0.34920.32860.81160.084*
O30.4262 (4)0.53679 (19)0.69827 (17)0.0576 (5)
C10.2532 (6)0.9244 (3)0.6413 (3)0.0591 (8)
H1A0.40860.93810.59790.071*
C20.1484 (7)1.0088 (3)0.7233 (3)0.0716 (9)
H2A0.23331.07890.73600.086*
C30.0811 (7)0.9900 (3)0.7866 (3)0.0787 (11)
H3A0.15261.04860.84090.094*
C40.2075 (6)0.8847 (4)0.7704 (3)0.0722 (9)
H4A0.36200.87130.81500.087*
C50.1023 (5)0.7988 (3)0.6870 (2)0.0539 (7)
H5A0.18700.72850.67460.065*
C60.1294 (5)0.8190 (2)0.6227 (2)0.0431 (6)
C70.2782 (4)0.4523 (3)0.6933 (2)0.0435 (6)
C80.2459 (5)0.7322 (3)0.5315 (2)0.0457 (6)
C90.1213 (4)0.6080 (3)0.5193 (2)0.0408 (6)
C100.1316 (4)0.4806 (2)0.5944 (2)0.0409 (6)
C110.0101 (5)0.3752 (3)0.5741 (2)0.0455 (6)
H11A0.01690.29040.62480.055*
O40.5524 (4)0.2728 (2)0.9206 (2)0.0761 (7)
O50.6987 (4)0.4786 (2)0.87190 (18)0.0693 (6)
H5B0.61010.48750.82130.104*
C120.8432 (6)0.3204 (4)1.0292 (3)0.0746 (9)
H12A0.74630.28441.10510.112*
H12B0.91580.40061.03800.112*
H12C0.96820.25161.00540.112*
C130.6874 (5)0.3584 (3)0.9348 (2)0.0550 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0554 (13)0.0830 (15)0.0741 (14)0.0221 (11)0.0045 (11)0.0151 (12)
O20.0595 (12)0.0610 (12)0.0512 (11)0.0098 (10)0.0240 (9)0.0006 (9)
O30.0590 (12)0.0525 (11)0.0673 (12)0.0059 (9)0.0279 (10)0.0067 (9)
C10.068 (2)0.0463 (15)0.0663 (18)0.0147 (14)0.0232 (15)0.0010 (14)
C20.094 (3)0.0463 (17)0.087 (2)0.0068 (17)0.040 (2)0.0154 (16)
C30.097 (3)0.061 (2)0.089 (2)0.0253 (19)0.040 (2)0.0350 (19)
C40.0526 (18)0.087 (2)0.080 (2)0.0086 (16)0.0105 (16)0.0297 (19)
C50.0420 (15)0.0573 (17)0.0663 (18)0.0045 (13)0.0100 (13)0.0194 (14)
C60.0446 (14)0.0385 (13)0.0483 (14)0.0016 (11)0.0159 (11)0.0055 (11)
C70.0431 (14)0.0430 (14)0.0446 (14)0.0032 (11)0.0108 (11)0.0085 (12)
C80.0395 (14)0.0492 (15)0.0492 (14)0.0030 (11)0.0150 (12)0.0028 (12)
C90.0349 (13)0.0474 (14)0.0413 (13)0.0009 (10)0.0072 (11)0.0123 (11)
C100.0380 (13)0.0455 (14)0.0409 (13)0.0007 (11)0.0095 (11)0.0115 (11)
C110.0507 (15)0.0431 (14)0.0439 (14)0.0011 (12)0.0143 (12)0.0063 (11)
O40.0871 (16)0.0680 (14)0.0820 (15)0.0102 (12)0.0425 (13)0.0038 (12)
O50.0718 (14)0.0687 (14)0.0695 (13)0.0067 (11)0.0297 (11)0.0022 (11)
C120.068 (2)0.090 (2)0.067 (2)0.0034 (18)0.0288 (16)0.0010 (17)
C130.0523 (17)0.0616 (18)0.0512 (16)0.0001 (14)0.0155 (13)0.0054 (14)
Geometric parameters (Å, º) top
O1—C81.217 (3)C6—C81.477 (4)
O2—C71.270 (3)C7—C101.491 (3)
O2—H2B0.8200C8—C91.520 (3)
O3—C71.259 (3)C9—C11i1.386 (3)
C1—C21.371 (4)C9—C101.392 (3)
C1—C61.383 (3)C10—C111.383 (3)
C1—H1A0.9300C11—C9i1.386 (3)
C2—C31.369 (5)C11—H11A0.9300
C2—H2A0.9300O4—C131.250 (3)
C3—C41.380 (5)O5—C131.273 (3)
C3—H3A0.9300O5—H5B0.8200
C4—C51.393 (4)C12—C131.488 (4)
C4—H4A0.9300C12—H12A0.9600
C5—C61.386 (4)C12—H12B0.9600
C5—H5A0.9300C12—H12C0.9600
C7—O2—H2B109.5O1—C8—C6122.5 (2)
C2—C1—C6120.5 (3)O1—C8—C9118.3 (2)
C2—C1—H1A119.8C6—C8—C9119.0 (2)
C6—C1—H1A119.8C11i—C9—C10118.7 (2)
C3—C2—C1120.0 (3)C11i—C9—C8116.7 (2)
C3—C2—H2A120.0C10—C9—C8124.6 (2)
C1—C2—H2A120.0C11—C10—C9119.2 (2)
C2—C3—C4120.6 (3)C11—C10—C7118.8 (2)
C2—C3—H3A119.7C9—C10—C7122.0 (2)
C4—C3—H3A119.7C10—C11—C9i122.1 (2)
C3—C4—C5119.6 (3)C10—C11—H11A119.0
C3—C4—H4A120.2C9i—C11—H11A119.0
C5—C4—H4A120.2C13—O5—H5B109.5
C6—C5—C4119.4 (3)C13—C12—H12A109.5
C6—C5—H5A120.3C13—C12—H12B109.5
C4—C5—H5A120.3H12A—C12—H12B109.5
C1—C6—C5119.8 (3)C13—C12—H12C109.5
C1—C6—C8118.9 (2)H12A—C12—H12C109.5
C5—C6—C8121.3 (2)H12B—C12—H12C109.5
O3—C7—O2123.6 (2)O4—C13—O5123.0 (3)
O3—C7—C10119.6 (2)O4—C13—C12119.4 (3)
O2—C7—C10116.8 (2)O5—C13—C12117.7 (3)
C6—C1—C2—C30.7 (4)C6—C8—C9—C11i99.2 (3)
C1—C2—C3—C41.3 (5)O1—C8—C9—C10103.5 (3)
C2—C3—C4—C51.4 (5)C6—C8—C9—C1081.0 (3)
C3—C4—C5—C61.0 (5)C11i—C9—C10—C110.3 (4)
C2—C1—C6—C50.2 (4)C8—C9—C10—C11180.0 (2)
C2—C1—C6—C8178.6 (3)C11i—C9—C10—C7177.2 (2)
C4—C5—C6—C10.4 (4)C8—C9—C10—C72.6 (4)
C4—C5—C6—C8178.7 (3)O3—C7—C10—C11166.2 (2)
C1—C6—C8—O110.6 (4)O2—C7—C10—C1113.3 (3)
C5—C6—C8—O1167.8 (3)O3—C7—C10—C911.2 (3)
C1—C6—C8—C9174.2 (2)O2—C7—C10—C9169.3 (2)
C5—C6—C8—C97.4 (4)C9—C10—C11—C9i0.3 (4)
O1—C8—C9—C11i76.2 (3)C7—C10—C11—C9i177.2 (2)
Symmetry code: (i) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2B···O40.821.822.633 (3)170
O5—H5B···O30.821.862.677 (3)171
 

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