Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026657/hk2264sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026657/hk2264Isup2.hkl |
CCDC reference: 654879
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.064
- wR factor = 0.197
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.02 PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 200 Ang. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT230_ALERT_2_C Hirshfeld Test Diff for C16 - C17 .. 5.55 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C29 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N2 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C22 H14 O6 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 C5 H5 N
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound, (I) was prepared by the literature method (Liu, Ji et al., 2006). The crystals were obtained by dissolving DBIA (1.5 g, 4.0 mmol) in pyridine (50 ml) and evaporating the solvent slowly at room temperature for about 15 d.
H atoms were positioned geometrically, with O—H = 0.82 Å (for OH) and C—H = 0.93 Å for aromatic H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.5 for OH H, and x = 1.2 for aromatic H atoms.
4,6-Dibenzoylisophthalic acid (DBIA) and its isomer 2,5-Dibenzoylterephthalic acid (DBTA), 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). DBTA tetrasolvate has been reported recently (Liu, Heng et al., 2006), and we herein report the crystal structure of the title compound, (I), which is of interest to us in the field of organic semiconductors.
The asymmetric unit of the title compound, (I), contains one DBIA and two pyridine molecules (Fig. 1), in which the bond lengths and angles are within normal ranges (Allen et al., 1987).
Rings A (C1—C6), B (C8—C13) and C (C17—C22) are, of course, planar and the dihedral angles between them are A/B = 73.3 (2)° and B/C = 105.0 (3)°.
In the crystal structure, intra- and intermolecular O—H···N and C—H···O hydrogen bonds (Table 1) link the molecules to form a three dimensional framework (Fig. 2), in which they may be effective in the stabilization of the structure.
For general background, see: Tonzola et al. (2003); Kolosov et al. (2002); Antoniadis et al. (1994); Allen et al. (1987). For related literature, see: Liu, Heng et al. (2006); Liu, Ji et al. (2006).
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.
C22H14O6·2C5H5N | Z = 2 |
Mr = 532.53 | F(000) = 556 |
Triclinic, P1 | Dx = 1.304 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.257 (2) Å | Cell parameters from 25 reflections |
b = 11.228 (2) Å | θ = 10–13° |
c = 12.109 (2) Å | µ = 0.09 mm−1 |
α = 101.37 (3)° | T = 298 K |
β = 97.17 (3)° | Plate, colorless |
γ = 90.32 (3)° | 0.40 × 0.30 × 0.20 mm |
V = 1355.8 (5) Å3 |
Enraf-Nonius CAD-4 diffractometer | 3172 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 26.0°, θmin = 1.7° |
ω/2θ scans | h = −12→12 |
Absorption correction: ψ scan (North et al., 1968) | k = −13→13 |
Tmin = 0.935, Tmax = 0.962 | l = 0→14 |
5635 measured reflections | 3 standard reflections every 120 min |
5322 independent reflections | intensity decay: 1% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.197 | w = 1/[σ2(Fo2) + (0.06P)2 + 1.5P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
5322 reflections | Δρmax = 0.29 e Å−3 |
361 parameters | Δρmin = −0.25 e Å−3 |
Primary atom site location: structure-invariant direct methods |
C22H14O6·2C5H5N | γ = 90.32 (3)° |
Mr = 532.53 | V = 1355.8 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.257 (2) Å | Mo Kα radiation |
b = 11.228 (2) Å | µ = 0.09 mm−1 |
c = 12.109 (2) Å | T = 298 K |
α = 101.37 (3)° | 0.40 × 0.30 × 0.20 mm |
β = 97.17 (3)° |
Enraf-Nonius CAD-4 diffractometer | 3172 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.026 |
Tmin = 0.935, Tmax = 0.962 | 3 standard reflections every 120 min |
5635 measured reflections | intensity decay: 1% |
5322 independent reflections |
R[F2 > 2σ(F2)] = 0.064 | 361 parameters |
wR(F2) = 0.197 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.29 e Å−3 |
5322 reflections | Δρmin = −0.25 e Å−3 |
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 | ||
O1 | −0.3679 (3) | −0.3363 (2) | 0.2543 (2) | 0.0784 (9) | |
O2 | −0.4109 (3) | −0.1895 (2) | 0.3963 (2) | 0.0687 (8) | |
H2B | −0.4594 | −0.2424 | 0.4085 | 0.103* | |
O3 | −0.2067 (3) | −0.3431 (2) | 0.0336 (2) | 0.0741 (8) | |
O4 | −0.1013 (3) | 0.1444 (2) | 0.5193 (2) | 0.0730 (8) | |
H4A | −0.0724 | 0.2065 | 0.5636 | 0.109* | |
O5 | −0.0046 (3) | 0.2261 (2) | 0.3967 (2) | 0.0708 (8) | |
O6 | −0.0130 (3) | 0.1521 (2) | 0.1154 (2) | 0.0663 (7) | |
N1 | 0.0531 (3) | 0.6687 (3) | 0.3228 (3) | 0.0623 (8) | |
N2 | −0.5820 (3) | −0.3480 (3) | 0.4331 (3) | 0.0675 (9) | |
C1 | −0.6799 (4) | −0.2681 (4) | −0.0675 (4) | 0.0854 (14) | |
H1A | −0.7676 | −0.2688 | −0.0986 | 0.102* | |
C2 | −0.6243 (5) | −0.1657 (4) | 0.0075 (4) | 0.0809 (13) | |
H2A | −0.6742 | −0.0974 | 0.0258 | 0.097* | |
C3 | −0.4958 (4) | −0.1652 (3) | 0.0546 (3) | 0.0649 (10) | |
H3A | −0.4595 | −0.0964 | 0.1054 | 0.078* | |
C4 | −0.4187 (3) | −0.2652 (3) | 0.0279 (3) | 0.0490 (8) | |
C5 | −0.4770 (4) | −0.3669 (3) | −0.0493 (3) | 0.0587 (9) | |
H5A | −0.4274 | −0.4350 | −0.0695 | 0.070* | |
C6 | −0.6067 (5) | −0.3673 (4) | −0.0955 (4) | 0.0779 (13) | |
H6A | −0.6443 | −0.4357 | −0.1460 | 0.093* | |
C7 | −0.2795 (4) | −0.2672 (3) | 0.0743 (3) | 0.0503 (8) | |
C8 | −0.2242 (3) | −0.1645 (3) | 0.1685 (3) | 0.0466 (8) | |
C9 | −0.2594 (3) | −0.1451 (3) | 0.2787 (3) | 0.0458 (8) | |
C10 | −0.2073 (3) | −0.0454 (3) | 0.3578 (3) | 0.0446 (8) | |
H10A | −0.2332 | −0.0317 | 0.4300 | 0.054* | |
C11 | −0.1176 (3) | 0.0352 (3) | 0.3330 (2) | 0.0434 (7) | |
C12 | −0.0790 (3) | 0.0147 (3) | 0.2245 (3) | 0.0459 (8) | |
C13 | −0.1306 (3) | −0.0853 (3) | 0.1442 (3) | 0.0476 (8) | |
H13A | −0.1025 | −0.1001 | 0.0727 | 0.057* | |
C14 | −0.3510 (4) | −0.2336 (3) | 0.3083 (3) | 0.0527 (9) | |
C15 | −0.0682 (3) | 0.1453 (3) | 0.4200 (3) | 0.0458 (8) | |
C16 | 0.0225 (4) | 0.0921 (3) | 0.1880 (3) | 0.0485 (8) | |
C17 | 0.1639 (3) | 0.0816 (3) | 0.2292 (3) | 0.0435 (7) | |
C18 | 0.2573 (4) | 0.1473 (3) | 0.1907 (3) | 0.0542 (9) | |
H18A | 0.2316 | 0.1989 | 0.1411 | 0.065* | |
C19 | 0.3880 (4) | 0.1357 (4) | 0.2264 (3) | 0.0645 (10) | |
H19A | 0.4508 | 0.1799 | 0.2008 | 0.077* | |
C20 | 0.4278 (4) | 0.0590 (4) | 0.3000 (3) | 0.0675 (11) | |
H20A | 0.5166 | 0.0517 | 0.3238 | 0.081* | |
C21 | 0.3347 (4) | −0.0057 (4) | 0.3371 (3) | 0.0655 (10) | |
H21A | 0.3608 | −0.0576 | 0.3863 | 0.079* | |
C22 | 0.2039 (4) | 0.0046 (3) | 0.3030 (3) | 0.0576 (9) | |
H22A | 0.1418 | −0.0399 | 0.3291 | 0.069* | |
C23 | −0.0048 (5) | 0.5690 (4) | 0.3389 (4) | 0.0759 (12) | |
H23A | −0.0385 | 0.5708 | 0.4070 | 0.091* | |
C24 | 0.1015 (5) | 0.6645 (4) | 0.2258 (3) | 0.0703 (11) | |
H24A | 0.1399 | 0.7350 | 0.2131 | 0.084* | |
C25 | 0.0979 (5) | 0.5611 (4) | 0.1431 (3) | 0.0753 (12) | |
H25A | 0.1363 | 0.5600 | 0.0773 | 0.090* | |
C26 | 0.0355 (5) | 0.4595 (4) | 0.1612 (4) | 0.0797 (13) | |
H26A | 0.0295 | 0.3883 | 0.1062 | 0.096* | |
C27 | −0.0172 (5) | 0.4627 (4) | 0.2588 (4) | 0.0798 (12) | |
H27A | −0.0607 | 0.3946 | 0.2713 | 0.096* | |
C28 | −0.7248 (6) | −0.5425 (6) | 0.4630 (7) | 0.116 (2) | |
H28A | −0.7713 | −0.6101 | 0.4730 | 0.139* | |
C29 | −0.7039 (6) | −0.4422 (7) | 0.5502 (5) | 0.122 (2) | |
H29A | −0.7366 | −0.4389 | 0.6190 | 0.146* | |
C30 | −0.6308 (5) | −0.3460 (5) | 0.5291 (4) | 0.0898 (14) | |
H30A | −0.6156 | −0.2766 | 0.5859 | 0.108* | |
C31 | −0.6069 (5) | −0.4462 (4) | 0.3544 (4) | 0.0883 (14) | |
H31A | −0.5727 | −0.4502 | 0.2861 | 0.106* | |
C32 | −0.6802 (5) | −0.5432 (5) | 0.3672 (6) | 0.1088 (18) | |
H32A | −0.6982 | −0.6095 | 0.3075 | 0.131* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.118 (2) | 0.0478 (15) | 0.0708 (18) | −0.0187 (15) | 0.0389 (17) | 0.0001 (13) |
O2 | 0.0842 (19) | 0.0604 (16) | 0.0631 (16) | −0.0150 (14) | 0.0312 (14) | 0.0028 (13) |
O3 | 0.0728 (18) | 0.0655 (17) | 0.0730 (18) | 0.0103 (14) | 0.0108 (14) | −0.0139 (14) |
O4 | 0.119 (2) | 0.0563 (16) | 0.0420 (14) | −0.0208 (15) | 0.0247 (14) | −0.0031 (12) |
O5 | 0.103 (2) | 0.0528 (15) | 0.0559 (15) | −0.0217 (15) | 0.0264 (15) | 0.0002 (12) |
O6 | 0.0717 (18) | 0.0716 (17) | 0.0627 (16) | −0.0037 (14) | 0.0056 (13) | 0.0328 (14) |
N1 | 0.079 (2) | 0.0567 (18) | 0.0489 (17) | −0.0001 (16) | 0.0137 (15) | 0.0009 (14) |
N2 | 0.068 (2) | 0.067 (2) | 0.069 (2) | −0.0097 (17) | 0.0082 (17) | 0.0155 (17) |
C1 | 0.060 (3) | 0.083 (3) | 0.099 (4) | −0.005 (2) | −0.010 (2) | −0.003 (3) |
C2 | 0.074 (3) | 0.072 (3) | 0.087 (3) | 0.011 (2) | 0.003 (2) | −0.003 (2) |
C3 | 0.065 (3) | 0.054 (2) | 0.067 (2) | 0.0021 (19) | 0.008 (2) | −0.0087 (18) |
C4 | 0.058 (2) | 0.0468 (19) | 0.0415 (18) | −0.0025 (16) | 0.0085 (15) | 0.0059 (15) |
C5 | 0.071 (3) | 0.047 (2) | 0.053 (2) | −0.0035 (18) | 0.0022 (18) | 0.0011 (16) |
C6 | 0.081 (3) | 0.059 (3) | 0.082 (3) | −0.016 (2) | −0.008 (2) | −0.002 (2) |
C7 | 0.065 (2) | 0.0440 (19) | 0.0432 (18) | −0.0019 (17) | 0.0182 (17) | 0.0043 (15) |
C8 | 0.057 (2) | 0.0430 (18) | 0.0377 (17) | −0.0001 (15) | 0.0048 (15) | 0.0037 (14) |
C9 | 0.053 (2) | 0.0407 (17) | 0.0435 (18) | 0.0023 (15) | 0.0080 (15) | 0.0058 (14) |
C10 | 0.0514 (19) | 0.0470 (18) | 0.0356 (16) | −0.0001 (15) | 0.0090 (14) | 0.0066 (14) |
C11 | 0.054 (2) | 0.0428 (17) | 0.0339 (16) | 0.0024 (15) | 0.0096 (14) | 0.0062 (13) |
C12 | 0.056 (2) | 0.0410 (17) | 0.0415 (17) | 0.0003 (15) | 0.0100 (15) | 0.0080 (14) |
C13 | 0.052 (2) | 0.053 (2) | 0.0372 (17) | 0.0005 (16) | 0.0118 (14) | 0.0029 (15) |
C14 | 0.065 (2) | 0.049 (2) | 0.0455 (19) | −0.0018 (17) | 0.0131 (17) | 0.0087 (16) |
C15 | 0.055 (2) | 0.0478 (19) | 0.0354 (17) | −0.0005 (16) | 0.0102 (14) | 0.0084 (14) |
C16 | 0.067 (2) | 0.0433 (18) | 0.0349 (17) | −0.0004 (16) | 0.0075 (15) | 0.0074 (14) |
C17 | 0.0504 (19) | 0.0414 (17) | 0.0373 (16) | −0.0013 (14) | 0.0079 (14) | 0.0030 (13) |
C18 | 0.063 (2) | 0.051 (2) | 0.048 (2) | −0.0081 (17) | 0.0066 (17) | 0.0084 (16) |
C19 | 0.062 (3) | 0.064 (2) | 0.067 (2) | −0.0138 (19) | 0.017 (2) | 0.006 (2) |
C20 | 0.060 (2) | 0.070 (3) | 0.068 (3) | 0.001 (2) | 0.013 (2) | 0.002 (2) |
C21 | 0.074 (3) | 0.069 (3) | 0.056 (2) | 0.013 (2) | 0.008 (2) | 0.0183 (19) |
C22 | 0.066 (3) | 0.054 (2) | 0.058 (2) | 0.0003 (18) | 0.0165 (18) | 0.0176 (18) |
C23 | 0.093 (3) | 0.074 (3) | 0.059 (2) | −0.010 (2) | 0.018 (2) | 0.004 (2) |
C24 | 0.105 (3) | 0.055 (2) | 0.053 (2) | 0.001 (2) | 0.013 (2) | 0.0112 (17) |
C25 | 0.107 (3) | 0.068 (3) | 0.048 (2) | 0.003 (2) | 0.016 (2) | 0.0007 (18) |
C26 | 0.105 (3) | 0.055 (2) | 0.067 (3) | 0.003 (2) | 0.003 (2) | −0.009 (2) |
C27 | 0.091 (3) | 0.060 (2) | 0.084 (3) | −0.012 (2) | 0.008 (2) | 0.007 (2) |
C28 | 0.097 (4) | 0.097 (4) | 0.167 (5) | −0.015 (3) | 0.007 (4) | 0.066 (4) |
C29 | 0.100 (4) | 0.170 (5) | 0.105 (4) | −0.043 (4) | 0.011 (3) | 0.055 (4) |
C30 | 0.080 (3) | 0.121 (4) | 0.066 (3) | −0.027 (3) | 0.008 (2) | 0.014 (3) |
C31 | 0.077 (3) | 0.084 (3) | 0.096 (3) | −0.015 (2) | 0.016 (3) | −0.004 (3) |
C32 | 0.086 (4) | 0.074 (3) | 0.155 (5) | −0.007 (3) | 0.010 (3) | −0.002 (3) |
O1—C14 | 1.208 (4) | C17—C18 | 1.386 (4) |
O2—C14 | 1.310 (4) | C17—C22 | 1.390 (5) |
O2—H2B | 0.8200 | C18—C19 | 1.371 (5) |
O3—C7 | 1.208 (4) | C18—H18A | 0.9300 |
O4—C15 | 1.292 (4) | C19—C20 | 1.384 (6) |
O4—H4A | 0.8200 | C19—H19A | 0.9300 |
O5—C15 | 1.212 (4) | C20—C21 | 1.368 (5) |
O6—C16 | 1.231 (4) | C20—H20A | 0.9300 |
C1—C6 | 1.358 (6) | C21—C22 | 1.365 (5) |
C1—C2 | 1.387 (6) | C21—H21A | 0.9300 |
C1—H1A | 0.9300 | C22—H22A | 0.9300 |
C2—C3 | 1.369 (6) | N1—C24 | 1.324 (5) |
C2—H2A | 0.9300 | N1—C23 | 1.324 (5) |
C3—C4 | 1.386 (5) | N2—C31 | 1.308 (5) |
C3—H3A | 0.9300 | N2—C30 | 1.318 (5) |
C4—C5 | 1.403 (5) | C23—C27 | 1.376 (6) |
C4—C7 | 1.470 (5) | C23—H23A | 0.9300 |
C5—C6 | 1.377 (6) | C24—C25 | 1.372 (5) |
C5—H5A | 0.9300 | C24—H24A | 0.9300 |
C6—H6A | 0.9300 | C25—C26 | 1.373 (6) |
C7—C8 | 1.506 (4) | C25—H25A | 0.9300 |
C8—C9 | 1.402 (4) | C26—C27 | 1.354 (6) |
C8—C13 | 1.401 (4) | C26—H26A | 0.9300 |
C9—C10 | 1.378 (4) | C27—H27A | 0.9300 |
C9—C14 | 1.487 (5) | C28—C32 | 1.298 (8) |
C10—C11 | 1.386 (4) | C28—C29 | 1.379 (8) |
C10—H10A | 0.9300 | C28—H28A | 0.9300 |
C11—C12 | 1.395 (4) | C29—C30 | 1.392 (7) |
C11—C15 | 1.497 (4) | C29—H29A | 0.9300 |
C12—C13 | 1.386 (4) | C30—H30A | 0.9300 |
C12—C16 | 1.514 (5) | C31—C32 | 1.364 (7) |
C13—H13A | 0.9300 | C31—H31A | 0.9300 |
C16—C17 | 1.487 (5) | C32—H32A | 0.9300 |
C14—O2—H2B | 109.5 | C18—C17—C22 | 119.6 (3) |
C15—O4—H4A | 109.5 | C18—C17—C16 | 119.2 (3) |
C6—C1—C2 | 120.2 (4) | C22—C17—C16 | 121.2 (3) |
C6—C1—H1A | 119.9 | C19—C18—C17 | 119.4 (3) |
C2—C1—H1A | 119.9 | C19—C18—H18A | 120.3 |
C3—C2—C1 | 119.9 (4) | C17—C18—H18A | 120.3 |
C3—C2—H2A | 120.0 | C18—C19—C20 | 121.0 (4) |
C1—C2—H2A | 120.0 | C18—C19—H19A | 119.5 |
C2—C3—C4 | 121.2 (4) | C20—C19—H19A | 119.5 |
C2—C3—H3A | 119.4 | C21—C20—C19 | 119.1 (4) |
C4—C3—H3A | 119.4 | C21—C20—H20A | 120.4 |
C5—C4—C3 | 117.7 (3) | C19—C20—H20A | 120.4 |
C5—C4—C7 | 119.4 (3) | C22—C21—C20 | 121.0 (4) |
C3—C4—C7 | 122.9 (3) | C22—C21—H21A | 119.5 |
C6—C5—C4 | 120.9 (4) | C20—C21—H21A | 119.5 |
C6—C5—H5A | 119.6 | C21—C22—C17 | 119.9 (3) |
C4—C5—H5A | 119.6 | C21—C22—H22A | 120.0 |
C1—C6—C5 | 120.2 (4) | C17—C22—H22A | 120.0 |
C1—C6—H6A | 119.9 | C24—N1—C23 | 118.1 (3) |
C5—C6—H6A | 119.9 | C31—N2—C30 | 116.7 (4) |
O3—C7—C4 | 122.1 (3) | N1—C23—C27 | 122.6 (4) |
O3—C7—C8 | 119.3 (3) | N1—C23—H23A | 118.7 |
C4—C7—C8 | 118.3 (3) | C27—C23—H23A | 118.7 |
C9—C8—C13 | 118.6 (3) | N1—C24—C25 | 123.2 (4) |
C9—C8—C7 | 123.8 (3) | N1—C24—H24A | 118.4 |
C13—C8—C7 | 117.6 (3) | C25—C24—H24A | 118.4 |
C10—C9—C8 | 119.4 (3) | C24—C25—C26 | 117.5 (4) |
C10—C9—C14 | 121.3 (3) | C24—C25—H25A | 121.2 |
C8—C9—C14 | 119.3 (3) | C26—C25—H25A | 121.2 |
C9—C10—C11 | 122.1 (3) | C27—C26—C25 | 120.2 (4) |
C9—C10—H10A | 119.0 | C27—C26—H26A | 119.9 |
C11—C10—H10A | 119.0 | C25—C26—H26A | 119.9 |
C12—C11—C10 | 118.9 (3) | C26—C27—C23 | 118.4 (4) |
C12—C11—C15 | 120.8 (3) | C26—C27—H27A | 120.8 |
C10—C11—C15 | 120.2 (3) | C23—C27—H27A | 120.8 |
C11—C12—C13 | 119.6 (3) | C32—C28—C29 | 120.5 (6) |
C11—C12—C16 | 124.3 (3) | C32—C28—H28A | 119.8 |
C13—C12—C16 | 116.0 (3) | C29—C28—H28A | 119.8 |
C12—C13—C8 | 121.3 (3) | C30—C29—C28 | 116.0 (6) |
C12—C13—H13A | 119.4 | C30—C29—H29A | 122.0 |
C8—C13—H13A | 119.4 | C28—C29—H29A | 122.0 |
O1—C14—O2 | 124.0 (3) | N2—C30—C29 | 123.6 (5) |
O1—C14—C9 | 122.0 (3) | N2—C30—H30A | 118.2 |
O2—C14—C9 | 114.0 (3) | C29—C30—H30A | 118.2 |
O5—C15—O4 | 124.8 (3) | N2—C31—C32 | 123.4 (5) |
O5—C15—C11 | 122.0 (3) | N2—C31—H31A | 118.3 |
O4—C15—C11 | 113.2 (3) | C32—C31—H31A | 118.3 |
O6—C16—C17 | 121.5 (3) | C28—C32—C31 | 119.8 (6) |
O6—C16—C12 | 118.8 (3) | C28—C32—H32A | 120.1 |
C17—C16—C12 | 119.2 (3) | C31—C32—H32A | 120.1 |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2B···N2 | 0.82 | 1.81 | 2.630 (4) | 173 |
O4—H4A···N1i | 0.82 | 1.75 | 2.544 (4) | 163 |
C10—H10A···O4 | 0.93 | 2.38 | 2.711 (4) | 101 |
C22—H22A···O4ii | 0.93 | 2.44 | 3.241 (4) | 144 |
C31—H31A···O1 | 0.93 | 2.56 | 3.209 (6) | 127 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C22H14O6·2C5H5N |
Mr | 532.53 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 10.257 (2), 11.228 (2), 12.109 (2) |
α, β, γ (°) | 101.37 (3), 97.17 (3), 90.32 (3) |
V (Å3) | 1355.8 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.40 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.935, 0.962 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5635, 5322, 3172 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.197, 1.03 |
No. of reflections | 5322 |
No. of parameters | 361 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.25 |
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 |
O2—H2B···N2 | 0.82 | 1.81 | 2.630 (4) | 173.00 |
O4—H4A···N1i | 0.82 | 1.75 | 2.544 (4) | 163.00 |
C10—H10A···O4 | 0.93 | 2.38 | 2.711 (4) | 101.00 |
C22—H22A···O4ii | 0.93 | 2.44 | 3.241 (4) | 144.00 |
C31—H31A···O1 | 0.93 | 2.56 | 3.209 (6) | 127.00 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y, −z+1. |
4,6-Dibenzoylisophthalic acid (DBIA) and its isomer 2,5-Dibenzoylterephthalic acid (DBTA), 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). DBTA tetrasolvate has been reported recently (Liu, Heng et al., 2006), and we herein report the crystal structure of the title compound, (I), which is of interest to us in the field of organic semiconductors.
The asymmetric unit of the title compound, (I), contains one DBIA and two pyridine molecules (Fig. 1), in which the bond lengths and angles are within normal ranges (Allen et al., 1987).
Rings A (C1—C6), B (C8—C13) and C (C17—C22) are, of course, planar and the dihedral angles between them are A/B = 73.3 (2)° and B/C = 105.0 (3)°.
In the crystal structure, intra- and intermolecular O—H···N and C—H···O hydrogen bonds (Table 1) link the molecules to form a three dimensional framework (Fig. 2), in which they may be effective in the stabilization of the structure.