2,5-Dibenzoyl­terephthalic acid dihydrate

The asymmetric unit of the title compound, C₂₂H₁₄O₆·2H₂O, contains one-half of a centrosymmetric 2,5-dibenzoyl­terephthalic acid mol­ecule and one water mol­ecule, held together by intra­molecular O—H...O hydrogen bonds. The dihedral angle between the central and outer rings is 108.8 (2)°. In the crystal structure, inter­molecular O—H...O hydrogen bonds link the mol­ecules to form a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.061
• wR factor = 0.200
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6
PLAT417_ALERT_2_C Short Inter D-H..H-D       HWB    ..  H3B     ..       2.12 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported HWB    ..  O2      ..       2.94 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.848(19) ......       2.11 su-Ra
              O1#  -H2#     1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
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S1. Comment

2,5-Dibenzoylterephthalic acid (DBTA) and its isomer 4,6-dibenzoylisophthalic acid (DBIA), can be utilized to synthesize organic semiconductors and conjugated polymers (Tonzola et al., 2003), which are of wide current interest for applications in electronic and optoelectronic devices including light-emitting diodes (Kolosov et al., 2002), thin film transistors and photovoltaic cells (Antoniadis et al., 1994). We report herein the crystal structure of the title compound, (I).

The asymmetric unit of the title compound, (I), contains one half of the 2,5-dibenzoylterephthalic acid molecule and one water molecule (Fig. 1), in which they are held together by intramolecular O—H···O hydrogen bonds (Table 1). The bond lengths and angles are generally within normal ranges (Allen et al., 1987). The rings A(C1—C6)and B(C8—C10/C8A—C10A) are, of course, planar and the dihedral angle between them is 108.8 (2)°, which is different significantly from the corresponding dihedral angles of 85.1 (1)° in DBTA acetic acid disolvate (Liu, Zhu et al., 2006), and 83.85 (3)° in DBTA pyridine tetrasolvate (Liu, Heng et al., 2006), probably due to the intramolecular O—H···O hydrogen bonds in (I).

In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 1) link the molecules to form a three dimensional network (Fig. 2), in which they seem to be effective in the stabilization of the structure.

Related literature

For general background, see: Tonzola et al. (2003); Kolosov et al. (2002); Antoniadis et al. (1994). For related literatue, see: Liu, Zhu et al. (2006); Liu, Heng et al. (2006); Liu, Ji et al. (2006). For bond- length data, see: Allen et al. (1987).

S2. Experimental

The title compound, (I), was prepared by the literature method (Liu, Ji et al., 2006). The crystals were obtained by dissolving DBTA (1.5 g, 4.0 mmol) in acetone (50 ml) with a few drops of water and evaporating the solvent slowly at room temperature for about 15 d.

S3. Refinement

H atoms (for OH and water) were located in difference syntheses and their positions were refined [O—H = 0.848 (19)–0.97 (5) Å and U_iso(H) = xU_eq(O), where x = 1.2 for water H and x = 1.5 for OH H atoms]. The remaining H atoms were positioned geometrically, with C—H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms, with U_iso(H) = 1.2U_eq(C).

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.

Figures

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines [symmetry code A: -x, -y, -z].
	Fig. 2. A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines.

2,5-Dibenzoylterephthalic acid dihydrate

Crystal data

C22H14O6·2H2O	Z = 1
Mr = 410.36	F(000) = 214
Triclinic, P1	Dx = 1.434 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7220 (11) Å	Cell parameters from 25 reflections
b = 8.0630 (16) Å	θ = 9–12°
c = 10.963 (2) Å	µ = 0.11 mm^−1
α = 102.74 (3)°	T = 298 K
β = 101.59 (3)°	Plate, colourless
γ = 97.49 (3)°	0.40 × 0.30 × 0.30 mm
V = 475.14 (19) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	1344 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
Graphite monochromator	θmax = 26.0°, θmin = 2.0°
ω/2θ scans	h = −7→6
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
Tmin = 0.957, Tmax = 0.968	l = 0→13
2056 measured reflections	3 standard reflections every 120 min
1857 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.200	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.06P)^2 + 1.5P] where P = (Fo^2 + 2Fc^2)/3
1857 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.38 e Å^−3
2 restraints	Δρmin = −0.47 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
OW	−0.1212 (6)	−0.4871 (4)	0.1929 (3)	0.0518 (8)
HWB	−0.275 (4)	−0.505 (7)	0.158 (5)	0.062*
HWA	−0.095 (9)	−0.390 (4)	0.176 (5)	0.062*
O1	0.0978 (5)	−0.1456 (4)	0.1920 (3)	0.0471 (8)
O2	0.3663 (5)	0.4355 (3)	0.0982 (3)	0.0478 (8)
O3	0.0816 (5)	0.2472 (4)	0.1329 (3)	0.0402 (7)
H3B	0.002 (9)	0.344 (7)	0.155 (5)	0.060*
C1	0.3251 (10)	0.2233 (7)	0.5483 (4)	0.0596 (13)
H1A	0.2314	0.2332	0.6089	0.072*
C2	0.5549 (10)	0.3219 (6)	0.5782 (4)	0.0568 (12)
H2A	0.6188	0.3945	0.6602	0.068*
C3	0.6902 (9)	0.3127 (6)	0.4862 (4)	0.0540 (12)
H3A	0.8431	0.3814	0.5054	0.065*
C4	0.5962 (8)	0.2005 (5)	0.3652 (4)	0.0427 (10)
H4A	0.6880	0.1930	0.3038	0.051*
C5	0.3682 (7)	0.1001 (5)	0.3351 (3)	0.0334 (8)
C6	0.2352 (8)	0.1105 (5)	0.4289 (4)	0.0463 (11)
H6A	0.0837	0.0402	0.4105	0.056*
C7	0.2633 (7)	−0.0260 (5)	0.2083 (3)	0.0337 (8)
C8	0.3820 (6)	−0.0090 (4)	0.0984 (3)	0.0282 (8)
C9	0.3948 (7)	0.1395 (4)	0.0501 (3)	0.0309 (8)
C10	0.5138 (7)	0.1452 (5)	−0.0477 (3)	0.0327 (8)
H10A	0.5236	0.2428	−0.0798	0.039*
C11	0.2797 (7)	0.2898 (4)	0.0967 (3)	0.0317 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
OW	0.0460 (17)	0.0390 (17)	0.072 (2)	0.0078 (14)	0.0242 (16)	0.0086 (15)
O1	0.0535 (18)	0.0395 (16)	0.0422 (16)	−0.0133 (13)	0.0214 (14)	0.0014 (12)
O2	0.0554 (18)	0.0273 (14)	0.070 (2)	0.0079 (12)	0.0388 (16)	0.0092 (13)
O3	0.0394 (15)	0.0353 (15)	0.0490 (17)	0.0061 (12)	0.0228 (13)	0.0065 (12)
C1	0.073 (3)	0.071 (3)	0.037 (2)	0.019 (3)	0.027 (2)	0.000 (2)
C2	0.076 (3)	0.047 (3)	0.037 (2)	0.008 (2)	0.013 (2)	−0.0086 (19)
C3	0.058 (3)	0.041 (2)	0.050 (3)	−0.003 (2)	0.004 (2)	0.000 (2)
C4	0.044 (2)	0.044 (2)	0.037 (2)	0.0030 (18)	0.0126 (17)	0.0049 (17)
C5	0.039 (2)	0.0338 (19)	0.0284 (18)	0.0058 (15)	0.0140 (15)	0.0051 (15)
C6	0.051 (3)	0.049 (2)	0.037 (2)	−0.0005 (19)	0.0256 (19)	−0.0011 (18)
C7	0.0341 (19)	0.0334 (19)	0.0322 (19)	−0.0014 (15)	0.0145 (15)	0.0037 (15)
C8	0.0328 (18)	0.0234 (16)	0.0266 (17)	0.0016 (13)	0.0131 (14)	−0.0010 (13)
C9	0.0370 (19)	0.0253 (17)	0.0277 (18)	0.0014 (14)	0.0123 (15)	−0.0003 (14)
C10	0.038 (2)	0.0299 (18)	0.0299 (18)	0.0044 (15)	0.0144 (15)	0.0026 (14)
C11	0.038 (2)	0.0273 (18)	0.0307 (18)	0.0111 (15)	0.0130 (15)	0.0010 (14)

Geometric parameters (Å, º)

OW—HWB	0.866 (19)	C5—C4	1.378 (5)
OW—HWA	0.85 (4)	C5—C6	1.391 (5)
O1—C7	1.215 (4)	C6—C1	1.374 (6)
O2—C11	1.209 (4)	C6—H6A	0.9300
O3—C11	1.304 (4)	C7—C5	1.486 (5)
O3—H3B	0.97 (5)	C7—C8	1.520 (5)
C1—H1A	0.9300	C8—C10^i	1.380 (5)
C2—C1	1.381 (7)	C9—C10	1.387 (5)
C2—H2A	0.9300	C9—C8	1.412 (5)
C3—C2	1.385 (7)	C9—C11	1.494 (5)
C3—H3A	0.9300	C10—C8^i	1.380 (5)
C4—C3	1.387 (6)	C10—H10A	0.9300
C4—H4A	0.9300
HWB—OW—HWA	93 (5)	C1—C6—H6A	119.6
C11—O3—H3B	113 (3)	C5—C6—H6A	119.6
C6—C1—C2	119.8 (4)	O1—C7—C5	122.7 (3)
C6—C1—H1A	120.1	O1—C7—C8	119.6 (3)
C2—C1—H1A	120.1	C5—C7—C8	117.5 (3)
C1—C2—C3	120.1 (4)	C10^i—C8—C9	119.8 (3)
C1—C2—H2A	120.0	C10^i—C8—C7	117.1 (3)
C3—C2—H2A	120.0	C9—C8—C7	123.0 (3)
C2—C3—C4	119.6 (4)	C10—C9—C8	118.8 (3)
C2—C3—H3A	120.2	C10—C9—C11	118.1 (3)
C4—C3—H3A	120.2	C8—C9—C11	123.1 (3)
C5—C4—C3	120.7 (4)	C8^i—C10—C9	121.4 (3)
C5—C4—H4A	119.7	C8^i—C10—H10A	119.3
C3—C4—H4A	119.7	C9—C10—H10A	119.3
C4—C5—C6	119.0 (4)	O2—C11—O3	124.8 (3)
C4—C5—C7	122.6 (3)	O2—C11—C9	121.4 (3)
C6—C5—C7	118.4 (3)	O3—C11—C9	113.7 (3)
C1—C6—C5	120.8 (4)
C8—C9—C10—C8^i	0.2 (6)	C5—C7—C8—C9	−61.4 (5)
C11—C9—C10—C8^i	−178.0 (3)	O1—C7—C5—C4	159.5 (4)
C10—C9—C11—O2	−32.9 (5)	C8—C7—C5—C4	−16.3 (6)
C8—C9—C11—O2	148.9 (4)	O1—C7—C5—C6	−17.3 (6)
C10—C9—C11—O3	146.5 (3)	C8—C7—C5—C6	166.9 (4)
C8—C9—C11—O3	−31.7 (5)	C6—C5—C4—C3	−1.2 (6)
C10—C9—C8—C10^i	−0.2 (6)	C7—C5—C4—C3	−178.0 (4)
C11—C9—C8—C10^i	177.9 (3)	C4—C5—C6—C1	2.3 (7)
C10—C9—C8—C7	178.0 (3)	C7—C5—C6—C1	179.2 (4)
C11—C9—C8—C7	−3.9 (5)	C5—C4—C3—C2	1.0 (7)
O1—C7—C8—C10^i	−59.1 (5)	C4—C3—C2—C1	−1.8 (7)
C5—C7—C8—C10^i	116.8 (4)	C5—C6—C1—C2	−3.1 (8)
O1—C7—C8—C9	122.6 (4)	C3—C2—C1—C6	2.8 (8)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···OW^ii	0.97 (5)	1.62 (5)	2.589 (4)	177 (5)
OW—HWB···O2^iii	0.87 (2)	1.98 (2)	2.842 (5)	171 (5)
OW—HWB···O2^iv	0.87 (2)	2.94 (5)	3.356 (5)	111 (4)
OW—HWA···O1	0.85 (2)	2.08 (3)	2.875 (4)	156 (5)

Symmetry codes: (ii) x, y+1, z; (iii) x−1, y−1, z; (iv) −x, −y, −z.