Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036707/hk2303sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036707/hk2303Isup2.hkl |
CCDC reference: 660337
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.061
- wR factor = 0.200
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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).
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.
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 Uiso(H) = xUeq(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 Uiso(H) = 1.2Ueq(C).
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.
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).
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.
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) Å3 |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.200 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.06P)2 + 1.5P] where P = (Fo2 + 2Fc2)/3 |
1857 reflections | (Δ/σ)max < 0.001 |
145 parameters | Δρmax = 0.38 e Å−3 |
2 restraints | Δρmin = −0.47 e Å−3 |
C22H14O6·2H2O | γ = 97.49 (3)° |
Mr = 410.36 | V = 475.14 (19) Å3 |
Triclinic, P1 | Z = 1 |
a = 5.7220 (11) Å | Mo Kα radiation |
b = 8.0630 (16) Å | µ = 0.11 mm−1 |
c = 10.963 (2) Å | T = 298 K |
α = 102.74 (3)° | 0.40 × 0.30 × 0.30 mm |
β = 101.59 (3)° |
Enraf–Nonius CAD-4 diffractometer | 1344 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.049 |
Tmin = 0.957, Tmax = 0.968 | 3 standard reflections every 120 min |
2056 measured reflections | intensity decay: none |
1857 independent reflections |
R[F2 > 2σ(F2)] = 0.061 | 2 restraints |
wR(F2) = 0.200 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.38 e Å−3 |
1857 reflections | Δρmin = −0.47 e Å−3 |
145 parameters |
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. |
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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—C10i | 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—C8i | 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) | C10i—C8—C9 | 119.8 (3) |
C1—C2—H2A | 120.0 | C10i—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) | C8i—C10—C9 | 121.4 (3) |
C5—C4—H4A | 119.7 | C8i—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—C8i | 0.2 (6) | C5—C7—C8—C9 | −61.4 (5) |
C11—C9—C10—C8i | −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—C10i | −0.2 (6) | C7—C5—C4—C3 | −178.0 (4) |
C11—C9—C8—C10i | 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—C10i | −59.1 (5) | C4—C3—C2—C1 | −1.8 (7) |
C5—C7—C8—C10i | 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. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3B···OWii | 0.97 (5) | 1.62 (5) | 2.589 (4) | 177 (5) |
OW—HWB···O2iii | 0.87 (2) | 1.98 (2) | 2.842 (5) | 171 (5) |
OW—HWB···O2iv | 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. |
Experimental details
Crystal data | |
Chemical formula | C22H14O6·2H2O |
Mr | 410.36 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 5.7220 (11), 8.0630 (16), 10.963 (2) |
α, β, γ (°) | 102.74 (3), 101.59 (3), 97.49 (3) |
V (Å3) | 475.14 (19) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.40 × 0.30 × 0.30 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.957, 0.968 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2056, 1857, 1344 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.200, 1.01 |
No. of reflections | 1857 |
No. of parameters | 145 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.38, −0.47 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1985), CAD-4 Software, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3B···OWi | 0.97 (5) | 1.62 (5) | 2.589 (4) | 177 (5) |
OW—HWB···O2ii | 0.866 (19) | 1.98 (2) | 2.842 (5) | 171 (5) |
OW—HWB···O2iii | 0.866 (19) | 2.94 (5) | 3.356 (5) | 111 (4) |
OW—HWA···O1 | 0.848 (19) | 2.08 (3) | 2.875 (4) | 156 (5) |
Symmetry codes: (i) x, y+1, z; (ii) x−1, y−1, z; (iii) −x, −y, −z. |
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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.