2,5-Dibenzoyl­terephthalic acid acetic acid disolvate

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.

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

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Computing details

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

Crystal data

C22H14O6·2C2H4O2	Z = 1
Mr = 494.44	F(000) = 258
Triclinic, P1	Dx = 1.344 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6380 (11) Å	Cell parameters from 25 reflections
b = 9.889 (2) Å	θ = 9–12°
c = 11.387 (2) Å	µ = 0.10 mm^−1
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) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	1453 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 26.0°, θmin = 1.9°
ω/2θ scans	h = −6→6
Absorption correction: ψ scan (North et al., 1968)	k = −11→12
Tmin = 0.959, Tmax = 0.979	l = 0→14
2388 measured reflections	3 standard reflections every 120 min
2388 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.169	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.09P)^2] where P = (Fo^2 + 2Fc^2)/3
2388 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.4308 (4)	0.7611 (2)	0.46037 (19)	0.0714 (6)
O2	0.2457 (3)	0.34137 (19)	0.76825 (16)	0.0561 (5)
H2B	0.3492	0.3286	0.8116	0.084*
O3	0.4262 (4)	0.53679 (19)	0.69827 (17)	0.0576 (5)
C1	0.2532 (6)	0.9244 (3)	0.6413 (3)	0.0591 (8)
H1A	0.4086	0.9381	0.5979	0.071*
C2	0.1484 (7)	1.0088 (3)	0.7233 (3)	0.0716 (9)
H2A	0.2333	1.0789	0.7360	0.086*
C3	−0.0811 (7)	0.9900 (3)	0.7866 (3)	0.0787 (11)
H3A	−0.1526	1.0486	0.8409	0.094*
C4	−0.2075 (6)	0.8847 (4)	0.7704 (3)	0.0722 (9)
H4A	−0.3620	0.8713	0.8150	0.087*
C5	−0.1023 (5)	0.7988 (3)	0.6870 (2)	0.0539 (7)
H5A	−0.1870	0.7285	0.6746	0.065*
C6	0.1294 (5)	0.8190 (2)	0.6227 (2)	0.0431 (6)
C7	0.2782 (4)	0.4523 (3)	0.6933 (2)	0.0435 (6)
C8	0.2459 (5)	0.7322 (3)	0.5315 (2)	0.0457 (6)
C9	0.1213 (4)	0.6080 (3)	0.5193 (2)	0.0408 (6)
C10	0.1316 (4)	0.4806 (2)	0.5944 (2)	0.0409 (6)
C11	0.0101 (5)	0.3752 (3)	0.5741 (2)	0.0455 (6)
H11A	0.0169	0.2904	0.6248	0.055*
O4	0.5524 (4)	0.2728 (2)	0.9206 (2)	0.0761 (7)
O5	0.6987 (4)	0.4786 (2)	0.87190 (18)	0.0693 (6)
H5B	0.6101	0.4875	0.8213	0.104*
C12	0.8432 (6)	0.3204 (4)	1.0292 (3)	0.0746 (9)
H12A	0.7463	0.2844	1.1051	0.112*
H12B	0.9158	0.4006	1.0380	0.112*
H12C	0.9682	0.2516	1.0054	0.112*
C13	0.6874 (5)	0.3584 (3)	0.9348 (2)	0.0550 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0554 (13)	0.0830 (15)	0.0741 (14)	−0.0221 (11)	0.0045 (11)	−0.0151 (12)
O2	0.0595 (12)	0.0610 (12)	0.0512 (11)	−0.0098 (10)	−0.0240 (9)	0.0006 (9)
O3	0.0590 (12)	0.0525 (11)	0.0673 (12)	−0.0059 (9)	−0.0279 (10)	−0.0067 (9)
C1	0.068 (2)	0.0463 (15)	0.0663 (18)	−0.0147 (14)	−0.0232 (15)	0.0010 (14)
C2	0.094 (3)	0.0463 (17)	0.087 (2)	−0.0068 (17)	−0.040 (2)	−0.0154 (16)
C3	0.097 (3)	0.061 (2)	0.089 (2)	0.0253 (19)	−0.040 (2)	−0.0350 (19)
C4	0.0526 (18)	0.087 (2)	0.080 (2)	0.0086 (16)	−0.0105 (16)	−0.0297 (19)
C5	0.0420 (15)	0.0573 (17)	0.0663 (18)	−0.0045 (13)	−0.0100 (13)	−0.0194 (14)
C6	0.0446 (14)	0.0385 (13)	0.0483 (14)	−0.0016 (11)	−0.0159 (11)	−0.0055 (11)
C7	0.0431 (14)	0.0430 (14)	0.0446 (14)	0.0032 (11)	−0.0108 (11)	−0.0085 (12)
C8	0.0395 (14)	0.0492 (15)	0.0492 (14)	−0.0030 (11)	−0.0150 (12)	−0.0028 (12)
C9	0.0349 (13)	0.0474 (14)	0.0413 (13)	0.0009 (10)	−0.0072 (11)	−0.0123 (11)
C10	0.0380 (13)	0.0455 (14)	0.0409 (13)	0.0007 (11)	−0.0095 (11)	−0.0115 (11)
C11	0.0507 (15)	0.0431 (14)	0.0439 (14)	0.0011 (12)	−0.0143 (12)	−0.0063 (11)
O4	0.0871 (16)	0.0680 (14)	0.0820 (15)	−0.0102 (12)	−0.0425 (13)	−0.0038 (12)
O5	0.0718 (14)	0.0687 (14)	0.0695 (13)	−0.0067 (11)	−0.0297 (11)	0.0022 (11)
C12	0.068 (2)	0.090 (2)	0.067 (2)	−0.0034 (18)	−0.0288 (16)	0.0010 (17)
C13	0.0523 (17)	0.0616 (18)	0.0512 (16)	−0.0001 (14)	−0.0155 (13)	−0.0054 (14)

Geometric parameters (Å, º)

O1—C8	1.217 (3)	C6—C8	1.477 (4)
O2—C7	1.270 (3)	C7—C10	1.491 (3)
O2—H2B	0.8200	C8—C9	1.520 (3)
O3—C7	1.259 (3)	C9—C11^i	1.386 (3)
C1—C2	1.371 (4)	C9—C10	1.392 (3)
C1—C6	1.383 (3)	C10—C11	1.383 (3)
C1—H1A	0.9300	C11—C9^i	1.386 (3)
C2—C3	1.369 (5)	C11—H11A	0.9300
C2—H2A	0.9300	O4—C13	1.250 (3)
C3—C4	1.380 (5)	O5—C13	1.273 (3)
C3—H3A	0.9300	O5—H5B	0.8200
C4—C5	1.393 (4)	C12—C13	1.488 (4)
C4—H4A	0.9300	C12—H12A	0.9600
C5—C6	1.386 (4)	C12—H12B	0.9600
C5—H5A	0.9300	C12—H12C	0.9600
C7—O2—H2B	109.5	O1—C8—C6	122.5 (2)
C2—C1—C6	120.5 (3)	O1—C8—C9	118.3 (2)
C2—C1—H1A	119.8	C6—C8—C9	119.0 (2)
C6—C1—H1A	119.8	C11^i—C9—C10	118.7 (2)
C3—C2—C1	120.0 (3)	C11^i—C9—C8	116.7 (2)
C3—C2—H2A	120.0	C10—C9—C8	124.6 (2)
C1—C2—H2A	120.0	C11—C10—C9	119.2 (2)
C2—C3—C4	120.6 (3)	C11—C10—C7	118.8 (2)
C2—C3—H3A	119.7	C9—C10—C7	122.0 (2)
C4—C3—H3A	119.7	C10—C11—C9^i	122.1 (2)
C3—C4—C5	119.6 (3)	C10—C11—H11A	119.0
C3—C4—H4A	120.2	C9^i—C11—H11A	119.0
C5—C4—H4A	120.2	C13—O5—H5B	109.5
C6—C5—C4	119.4 (3)	C13—C12—H12A	109.5
C6—C5—H5A	120.3	C13—C12—H12B	109.5
C4—C5—H5A	120.3	H12A—C12—H12B	109.5
C1—C6—C5	119.8 (3)	C13—C12—H12C	109.5
C1—C6—C8	118.9 (2)	H12A—C12—H12C	109.5
C5—C6—C8	121.3 (2)	H12B—C12—H12C	109.5
O3—C7—O2	123.6 (2)	O4—C13—O5	123.0 (3)
O3—C7—C10	119.6 (2)	O4—C13—C12	119.4 (3)
O2—C7—C10	116.8 (2)	O5—C13—C12	117.7 (3)
C6—C1—C2—C3	−0.7 (4)	C6—C8—C9—C11^i	99.2 (3)
C1—C2—C3—C4	1.3 (5)	O1—C8—C9—C10	103.5 (3)
C2—C3—C4—C5	−1.4 (5)	C6—C8—C9—C10	−81.0 (3)
C3—C4—C5—C6	1.0 (5)	C11^i—C9—C10—C11	−0.3 (4)
C2—C1—C6—C5	0.2 (4)	C8—C9—C10—C11	180.0 (2)
C2—C1—C6—C8	178.6 (3)	C11^i—C9—C10—C7	177.2 (2)
C4—C5—C6—C1	−0.4 (4)	C8—C9—C10—C7	−2.6 (4)
C4—C5—C6—C8	−178.7 (3)	O3—C7—C10—C11	166.2 (2)
C1—C6—C8—O1	−10.6 (4)	O2—C7—C10—C11	−13.3 (3)
C5—C6—C8—O1	167.8 (3)	O3—C7—C10—C9	−11.2 (3)
C1—C6—C8—C9	174.2 (2)	O2—C7—C10—C9	169.3 (2)
C5—C6—C8—C9	−7.4 (4)	C9—C10—C11—C9^i	0.3 (4)
O1—C8—C9—C11^i	−76.2 (3)	C7—C10—C11—C9^i	−177.2 (2)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O4	0.82	1.82	2.633 (3)	170
O5—H5B···O3	0.82	1.86	2.677 (3)	171