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The asymmetric unit of the title compound, C22H14O6·2C5H5N, contains one 4,6-dibenzoyl­isophthalic acid (DBIA) and two pyridine mol­ecules. The dihedral angles between the terminal phenyl rings and the central benzene ring are 73.3 (2) and 105.0 (3)°. In the crystal structure, there is an intra­mol­ecular C—H...O hydrogen bond; inter­molecular O—H...N and C—H...O hydrogen bonds link the mol­ecules to form a three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026657/hk2264sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026657/hk2264Isup2.hkl
Contains datablock I

CCDC reference: 654879

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Comment top

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.

Related literature top

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).

Experimental top

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.

Refinement top

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.

Structure description top

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).

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.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. Hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.
4,6-Dibenzoylisophthalic acid pyridine disolvate top
Crystal data top
C22H14O6·2C5H5NZ = 2
Mr = 532.53F(000) = 556
Triclinic, P1Dx = 1.304 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.257 (2) ÅCell parameters from 25 reflections
b = 11.228 (2) Åθ = 10–13°
c = 12.109 (2) ŵ = 0.09 mm1
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
Data collection top
Enraf-Nonius CAD-4
diffractometer
3172 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 26.0°, θmin = 1.7°
ω/2θ scansh = 1212
Absorption correction: ψ scan
(North et al., 1968)
k = 1313
Tmin = 0.935, Tmax = 0.962l = 014
5635 measured reflections3 standard reflections every 120 min
5322 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H-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 reflectionsΔρmax = 0.29 e Å3
361 parametersΔρmin = 0.25 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C22H14O6·2C5H5Nγ = 90.32 (3)°
Mr = 532.53V = 1355.8 (5) Å3
Triclinic, P1Z = 2
a = 10.257 (2) ÅMo Kα radiation
b = 11.228 (2) ŵ = 0.09 mm1
c = 12.109 (2) ÅT = 298 K
α = 101.37 (3)°0.40 × 0.30 × 0.20 mm
β = 97.17 (3)°
Data collection top
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 = 0.9623 standard reflections every 120 min
5635 measured reflections intensity decay: 1%
5322 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.064361 parameters
wR(F2) = 0.197H-atom parameters constrained
S = 1.03Δρmax = 0.29 e Å3
5322 reflectionsΔρmin = 0.25 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
O10.3679 (3)0.3363 (2)0.2543 (2)0.0784 (9)
O20.4109 (3)0.1895 (2)0.3963 (2)0.0687 (8)
H2B0.45940.24240.40850.103*
O30.2067 (3)0.3431 (2)0.0336 (2)0.0741 (8)
O40.1013 (3)0.1444 (2)0.5193 (2)0.0730 (8)
H4A0.07240.20650.56360.109*
O50.0046 (3)0.2261 (2)0.3967 (2)0.0708 (8)
O60.0130 (3)0.1521 (2)0.1154 (2)0.0663 (7)
N10.0531 (3)0.6687 (3)0.3228 (3)0.0623 (8)
N20.5820 (3)0.3480 (3)0.4331 (3)0.0675 (9)
C10.6799 (4)0.2681 (4)0.0675 (4)0.0854 (14)
H1A0.76760.26880.09860.102*
C20.6243 (5)0.1657 (4)0.0075 (4)0.0809 (13)
H2A0.67420.09740.02580.097*
C30.4958 (4)0.1652 (3)0.0546 (3)0.0649 (10)
H3A0.45950.09640.10540.078*
C40.4187 (3)0.2652 (3)0.0279 (3)0.0490 (8)
C50.4770 (4)0.3669 (3)0.0493 (3)0.0587 (9)
H5A0.42740.43500.06950.070*
C60.6067 (5)0.3673 (4)0.0955 (4)0.0779 (13)
H6A0.64430.43570.14600.093*
C70.2795 (4)0.2672 (3)0.0743 (3)0.0503 (8)
C80.2242 (3)0.1645 (3)0.1685 (3)0.0466 (8)
C90.2594 (3)0.1451 (3)0.2787 (3)0.0458 (8)
C100.2073 (3)0.0454 (3)0.3578 (3)0.0446 (8)
H10A0.23320.03170.43000.054*
C110.1176 (3)0.0352 (3)0.3330 (2)0.0434 (7)
C120.0790 (3)0.0147 (3)0.2245 (3)0.0459 (8)
C130.1306 (3)0.0853 (3)0.1442 (3)0.0476 (8)
H13A0.10250.10010.07270.057*
C140.3510 (4)0.2336 (3)0.3083 (3)0.0527 (9)
C150.0682 (3)0.1453 (3)0.4200 (3)0.0458 (8)
C160.0225 (4)0.0921 (3)0.1880 (3)0.0485 (8)
C170.1639 (3)0.0816 (3)0.2292 (3)0.0435 (7)
C180.2573 (4)0.1473 (3)0.1907 (3)0.0542 (9)
H18A0.23160.19890.14110.065*
C190.3880 (4)0.1357 (4)0.2264 (3)0.0645 (10)
H19A0.45080.17990.20080.077*
C200.4278 (4)0.0590 (4)0.3000 (3)0.0675 (11)
H20A0.51660.05170.32380.081*
C210.3347 (4)0.0057 (4)0.3371 (3)0.0655 (10)
H21A0.36080.05760.38630.079*
C220.2039 (4)0.0046 (3)0.3030 (3)0.0576 (9)
H22A0.14180.03990.32910.069*
C230.0048 (5)0.5690 (4)0.3389 (4)0.0759 (12)
H23A0.03850.57080.40700.091*
C240.1015 (5)0.6645 (4)0.2258 (3)0.0703 (11)
H24A0.13990.73500.21310.084*
C250.0979 (5)0.5611 (4)0.1431 (3)0.0753 (12)
H25A0.13630.56000.07730.090*
C260.0355 (5)0.4595 (4)0.1612 (4)0.0797 (13)
H26A0.02950.38830.10620.096*
C270.0172 (5)0.4627 (4)0.2588 (4)0.0798 (12)
H27A0.06070.39460.27130.096*
C280.7248 (6)0.5425 (6)0.4630 (7)0.116 (2)
H28A0.77130.61010.47300.139*
C290.7039 (6)0.4422 (7)0.5502 (5)0.122 (2)
H29A0.73660.43890.61900.146*
C300.6308 (5)0.3460 (5)0.5291 (4)0.0898 (14)
H30A0.61560.27660.58590.108*
C310.6069 (5)0.4462 (4)0.3544 (4)0.0883 (14)
H31A0.57270.45020.28610.106*
C320.6802 (5)0.5432 (5)0.3672 (6)0.1088 (18)
H32A0.69820.60950.30750.131*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.118 (2)0.0478 (15)0.0708 (18)0.0187 (15)0.0389 (17)0.0001 (13)
O20.0842 (19)0.0604 (16)0.0631 (16)0.0150 (14)0.0312 (14)0.0028 (13)
O30.0728 (18)0.0655 (17)0.0730 (18)0.0103 (14)0.0108 (14)0.0139 (14)
O40.119 (2)0.0563 (16)0.0420 (14)0.0208 (15)0.0247 (14)0.0031 (12)
O50.103 (2)0.0528 (15)0.0559 (15)0.0217 (15)0.0264 (15)0.0002 (12)
O60.0717 (18)0.0716 (17)0.0627 (16)0.0037 (14)0.0056 (13)0.0328 (14)
N10.079 (2)0.0567 (18)0.0489 (17)0.0001 (16)0.0137 (15)0.0009 (14)
N20.068 (2)0.067 (2)0.069 (2)0.0097 (17)0.0082 (17)0.0155 (17)
C10.060 (3)0.083 (3)0.099 (4)0.005 (2)0.010 (2)0.003 (3)
C20.074 (3)0.072 (3)0.087 (3)0.011 (2)0.003 (2)0.003 (2)
C30.065 (3)0.054 (2)0.067 (2)0.0021 (19)0.008 (2)0.0087 (18)
C40.058 (2)0.0468 (19)0.0415 (18)0.0025 (16)0.0085 (15)0.0059 (15)
C50.071 (3)0.047 (2)0.053 (2)0.0035 (18)0.0022 (18)0.0011 (16)
C60.081 (3)0.059 (3)0.082 (3)0.016 (2)0.008 (2)0.002 (2)
C70.065 (2)0.0440 (19)0.0432 (18)0.0019 (17)0.0182 (17)0.0043 (15)
C80.057 (2)0.0430 (18)0.0377 (17)0.0001 (15)0.0048 (15)0.0037 (14)
C90.053 (2)0.0407 (17)0.0435 (18)0.0023 (15)0.0080 (15)0.0058 (14)
C100.0514 (19)0.0470 (18)0.0356 (16)0.0001 (15)0.0090 (14)0.0066 (14)
C110.054 (2)0.0428 (17)0.0339 (16)0.0024 (15)0.0096 (14)0.0062 (13)
C120.056 (2)0.0410 (17)0.0415 (17)0.0003 (15)0.0100 (15)0.0080 (14)
C130.052 (2)0.053 (2)0.0372 (17)0.0005 (16)0.0118 (14)0.0029 (15)
C140.065 (2)0.049 (2)0.0455 (19)0.0018 (17)0.0131 (17)0.0087 (16)
C150.055 (2)0.0478 (19)0.0354 (17)0.0005 (16)0.0102 (14)0.0084 (14)
C160.067 (2)0.0433 (18)0.0349 (17)0.0004 (16)0.0075 (15)0.0074 (14)
C170.0504 (19)0.0414 (17)0.0373 (16)0.0013 (14)0.0079 (14)0.0030 (13)
C180.063 (2)0.051 (2)0.048 (2)0.0081 (17)0.0066 (17)0.0084 (16)
C190.062 (3)0.064 (2)0.067 (2)0.0138 (19)0.017 (2)0.006 (2)
C200.060 (2)0.070 (3)0.068 (3)0.001 (2)0.013 (2)0.002 (2)
C210.074 (3)0.069 (3)0.056 (2)0.013 (2)0.008 (2)0.0183 (19)
C220.066 (3)0.054 (2)0.058 (2)0.0003 (18)0.0165 (18)0.0176 (18)
C230.093 (3)0.074 (3)0.059 (2)0.010 (2)0.018 (2)0.004 (2)
C240.105 (3)0.055 (2)0.053 (2)0.001 (2)0.013 (2)0.0112 (17)
C250.107 (3)0.068 (3)0.048 (2)0.003 (2)0.016 (2)0.0007 (18)
C260.105 (3)0.055 (2)0.067 (3)0.003 (2)0.003 (2)0.009 (2)
C270.091 (3)0.060 (2)0.084 (3)0.012 (2)0.008 (2)0.007 (2)
C280.097 (4)0.097 (4)0.167 (5)0.015 (3)0.007 (4)0.066 (4)
C290.100 (4)0.170 (5)0.105 (4)0.043 (4)0.011 (3)0.055 (4)
C300.080 (3)0.121 (4)0.066 (3)0.027 (3)0.008 (2)0.014 (3)
C310.077 (3)0.084 (3)0.096 (3)0.015 (2)0.016 (3)0.004 (3)
C320.086 (4)0.074 (3)0.155 (5)0.007 (3)0.010 (3)0.002 (3)
Geometric parameters (Å, º) top
O1—C141.208 (4)C17—C181.386 (4)
O2—C141.310 (4)C17—C221.390 (5)
O2—H2B0.8200C18—C191.371 (5)
O3—C71.208 (4)C18—H18A0.9300
O4—C151.292 (4)C19—C201.384 (6)
O4—H4A0.8200C19—H19A0.9300
O5—C151.212 (4)C20—C211.368 (5)
O6—C161.231 (4)C20—H20A0.9300
C1—C61.358 (6)C21—C221.365 (5)
C1—C21.387 (6)C21—H21A0.9300
C1—H1A0.9300C22—H22A0.9300
C2—C31.369 (6)N1—C241.324 (5)
C2—H2A0.9300N1—C231.324 (5)
C3—C41.386 (5)N2—C311.308 (5)
C3—H3A0.9300N2—C301.318 (5)
C4—C51.403 (5)C23—C271.376 (6)
C4—C71.470 (5)C23—H23A0.9300
C5—C61.377 (6)C24—C251.372 (5)
C5—H5A0.9300C24—H24A0.9300
C6—H6A0.9300C25—C261.373 (6)
C7—C81.506 (4)C25—H25A0.9300
C8—C91.402 (4)C26—C271.354 (6)
C8—C131.401 (4)C26—H26A0.9300
C9—C101.378 (4)C27—H27A0.9300
C9—C141.487 (5)C28—C321.298 (8)
C10—C111.386 (4)C28—C291.379 (8)
C10—H10A0.9300C28—H28A0.9300
C11—C121.395 (4)C29—C301.392 (7)
C11—C151.497 (4)C29—H29A0.9300
C12—C131.386 (4)C30—H30A0.9300
C12—C161.514 (5)C31—C321.364 (7)
C13—H13A0.9300C31—H31A0.9300
C16—C171.487 (5)C32—H32A0.9300
C14—O2—H2B109.5C18—C17—C22119.6 (3)
C15—O4—H4A109.5C18—C17—C16119.2 (3)
C6—C1—C2120.2 (4)C22—C17—C16121.2 (3)
C6—C1—H1A119.9C19—C18—C17119.4 (3)
C2—C1—H1A119.9C19—C18—H18A120.3
C3—C2—C1119.9 (4)C17—C18—H18A120.3
C3—C2—H2A120.0C18—C19—C20121.0 (4)
C1—C2—H2A120.0C18—C19—H19A119.5
C2—C3—C4121.2 (4)C20—C19—H19A119.5
C2—C3—H3A119.4C21—C20—C19119.1 (4)
C4—C3—H3A119.4C21—C20—H20A120.4
C5—C4—C3117.7 (3)C19—C20—H20A120.4
C5—C4—C7119.4 (3)C22—C21—C20121.0 (4)
C3—C4—C7122.9 (3)C22—C21—H21A119.5
C6—C5—C4120.9 (4)C20—C21—H21A119.5
C6—C5—H5A119.6C21—C22—C17119.9 (3)
C4—C5—H5A119.6C21—C22—H22A120.0
C1—C6—C5120.2 (4)C17—C22—H22A120.0
C1—C6—H6A119.9C24—N1—C23118.1 (3)
C5—C6—H6A119.9C31—N2—C30116.7 (4)
O3—C7—C4122.1 (3)N1—C23—C27122.6 (4)
O3—C7—C8119.3 (3)N1—C23—H23A118.7
C4—C7—C8118.3 (3)C27—C23—H23A118.7
C9—C8—C13118.6 (3)N1—C24—C25123.2 (4)
C9—C8—C7123.8 (3)N1—C24—H24A118.4
C13—C8—C7117.6 (3)C25—C24—H24A118.4
C10—C9—C8119.4 (3)C24—C25—C26117.5 (4)
C10—C9—C14121.3 (3)C24—C25—H25A121.2
C8—C9—C14119.3 (3)C26—C25—H25A121.2
C9—C10—C11122.1 (3)C27—C26—C25120.2 (4)
C9—C10—H10A119.0C27—C26—H26A119.9
C11—C10—H10A119.0C25—C26—H26A119.9
C12—C11—C10118.9 (3)C26—C27—C23118.4 (4)
C12—C11—C15120.8 (3)C26—C27—H27A120.8
C10—C11—C15120.2 (3)C23—C27—H27A120.8
C11—C12—C13119.6 (3)C32—C28—C29120.5 (6)
C11—C12—C16124.3 (3)C32—C28—H28A119.8
C13—C12—C16116.0 (3)C29—C28—H28A119.8
C12—C13—C8121.3 (3)C30—C29—C28116.0 (6)
C12—C13—H13A119.4C30—C29—H29A122.0
C8—C13—H13A119.4C28—C29—H29A122.0
O1—C14—O2124.0 (3)N2—C30—C29123.6 (5)
O1—C14—C9122.0 (3)N2—C30—H30A118.2
O2—C14—C9114.0 (3)C29—C30—H30A118.2
O5—C15—O4124.8 (3)N2—C31—C32123.4 (5)
O5—C15—C11122.0 (3)N2—C31—H31A118.3
O4—C15—C11113.2 (3)C32—C31—H31A118.3
O6—C16—C17121.5 (3)C28—C32—C31119.8 (6)
O6—C16—C12118.8 (3)C28—C32—H32A120.1
C17—C16—C12119.2 (3)C31—C32—H32A120.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2B···N20.821.812.630 (4)173
O4—H4A···N1i0.821.752.544 (4)163
C10—H10A···O40.932.382.711 (4)101
C22—H22A···O4ii0.932.443.241 (4)144
C31—H31A···O10.932.563.209 (6)127
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC22H14O6·2C5H5N
Mr532.53
Crystal system, space groupTriclinic, 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)
V3)1355.8 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.40 × 0.30 × 0.20
Data collection
DiffractometerEnraf-Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.935, 0.962
No. of measured, independent and
observed [I > 2σ(I)] reflections
5635, 5322, 3172
Rint0.026
(sin θ/λ)max1)0.616
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.197, 1.03
No. of reflections5322
No. of parameters361
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2B···N20.821.812.630 (4)173.00
O4—H4A···N1i0.821.752.544 (4)163.00
C10—H10A···O40.932.382.711 (4)101.00
C22—H22A···O4ii0.932.443.241 (4)144.00
C31—H31A···O10.932.563.209 (6)127.00
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z+1.
 

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