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In the title compound, C14H8O6S, the dihedral angle of the two phthalic fragments is 76.41 (10) Å. The molecule lies on a mirror plane. The C atoms of the benzene rings have bond lengths in the range 1.384 (2)-1.490 (2) Å and bond angles in the range 118.80 (16)-121.64 (15)°. Centrosymmetric rings of hydrogen-bonded carboxyl groups connect mol­ecules into a zigzig chain.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021216/kp2097sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021216/kp2097Isup2.hkl
Contains datablock I

CCDC reference: 651414

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.104
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT245_ALERT_2_C U(iso) H1A Smaller than U(eq) O1 by ... 0.01 AngSq
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 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 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

Comment top

Recently, the design and synthesis of the metal-organic frameworks (MOFs) have led to a large number of coordination polymers (Moulton et al., 2001; Kitagawa et al., 2004; Yaghi et al., 2003). 4,4'-sulfonyldibenzoic acid is a typical V-shaped dicarboxylate ligand, which is important in construction of some novel frameworks (Jin et al., 2006; Chen et al., 2002). Here we report the crystal structure of (I) (Fig. 1). The central atom S1 has a tetrahedral arrangement, with the S1—O3=1.4353 (17) Å, S1—O4=1.4405 (18) Å. The atoms S1,O3 and O4 are located at the special position on the mirror plane (x,1/4 - y,z) and the molecular symmetry is Cm. An intermolecular O1—H1A···O2 hydrogen bond connects molecules into a infinite zigzag chain (Fig. 2).

Related literature top

For related literature, see: Chen & Lin (2002); Kitagawa & Kitaura (2004); Moulton & Zaworotko (2001); Fujita et al. (1994).

Experimental top

The title compound (I), was prepared by the hydrothermal reaction of Mn(OAc)2.4H2O(0.050 g, 0.20 mmol), 4,4'-sulfonyldibenzoic acid (0.062 g, 0.20 mmol) and in water (8 ml). The reaction was performed in 23 ml Teflon-lined stainless steel Parr bombs under autogeneous pressure. After heating at 423 K for 3 days and cooling to room temperature at 5 K h-1, green crystals of (I) were obtained.

Refinement top

The H atoms were positioned geometrically with C—H = 0.93 Å; they were constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq.

Structure description top

Recently, the design and synthesis of the metal-organic frameworks (MOFs) have led to a large number of coordination polymers (Moulton et al., 2001; Kitagawa et al., 2004; Yaghi et al., 2003). 4,4'-sulfonyldibenzoic acid is a typical V-shaped dicarboxylate ligand, which is important in construction of some novel frameworks (Jin et al., 2006; Chen et al., 2002). Here we report the crystal structure of (I) (Fig. 1). The central atom S1 has a tetrahedral arrangement, with the S1—O3=1.4353 (17) Å, S1—O4=1.4405 (18) Å. The atoms S1,O3 and O4 are located at the special position on the mirror plane (x,1/4 - y,z) and the molecular symmetry is Cm. An intermolecular O1—H1A···O2 hydrogen bond connects molecules into a infinite zigzag chain (Fig. 2).

For related literature, see: Chen & Lin (2002); Kitagawa & Kitaura (2004); Moulton & Zaworotko (2001); Fujita et al. (1994).

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. Crystal packing of (I), showing the hydrogen-bonded (dashed lines) chain. H atoms not involved in the hydrogen bonds have been omitted for clarity.
4,4'-Sulfonyldibenzoic acid top
Crystal data top
C14H10O6SF(000) = 316
Mr = 306.29Dx = 1.602 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
a = 5.0019 (4) ÅCell parameters from 1385 reflections
b = 23.3653 (17) Åθ = 2.6–27.5°
c = 5.7871 (5) ŵ = 0.28 mm1
β = 110.151 (3)°T = 293 K
V = 634.94 (9) Å3Prism, white
Z = 20.21 × 0.13 × 0.10 mm
Data collection top
Mercury CCD
diffractometer
1493 independent reflections
Radiation source: fine-focus sealed tube1287 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 14.6306 pixels mm-1θmax = 27.5°, θmin = 3.5°
CCD_Profile_fitting scansh = 66
Absorption correction: multi-scan
PROGRAM? (Reference?)
k = 3028
Tmin = 0.943, Tmax = 0.972l = 67
4922 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0437P)2 + 0.2393P]
where P = (Fo2 + 2Fc2)/3
1493 reflections(Δ/σ)max < 0.001
100 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C14H10O6SV = 634.94 (9) Å3
Mr = 306.29Z = 2
Monoclinic, P21/mMo Kα radiation
a = 5.0019 (4) ŵ = 0.28 mm1
b = 23.3653 (17) ÅT = 293 K
c = 5.7871 (5) Å0.21 × 0.13 × 0.10 mm
β = 110.151 (3)°
Data collection top
Mercury CCD
diffractometer
1493 independent reflections
Absorption correction: multi-scan
PROGRAM? (Reference?)
1287 reflections with I > 2σ(I)
Tmin = 0.943, Tmax = 0.972Rint = 0.023
4922 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 1.13Δρmax = 0.27 e Å3
1493 reflectionsΔρmin = 0.36 e Å3
100 parameters
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
S11.01179 (12)0.25000.38263 (11)0.02846 (19)
O10.0581 (3)0.04204 (6)0.2645 (3)0.0538 (4)
C10.2637 (4)0.05520 (7)0.4617 (3)0.0349 (4)
O20.3019 (3)0.03297 (6)0.6669 (3)0.0519 (4)
C20.4609 (4)0.10079 (7)0.4376 (3)0.0304 (4)
O31.2667 (4)0.25000.5955 (3)0.0379 (4)
C30.6752 (4)0.12019 (7)0.6472 (3)0.0347 (4)
H30.70430.10270.79820.042*
O41.0291 (4)0.25000.1392 (3)0.0380 (4)
C40.8453 (4)0.16565 (7)0.6310 (3)0.0331 (4)
H40.98680.17940.77090.040*
C50.8018 (3)0.19037 (6)0.4031 (3)0.0270 (4)
C60.5925 (4)0.17070 (7)0.1919 (3)0.0335 (4)
H60.56640.18760.04030.040*
C70.4233 (4)0.12549 (8)0.2107 (3)0.0353 (4)
H70.28320.11150.07030.042*
H1A0.07840.01810.27690.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0256 (3)0.0241 (3)0.0379 (4)0.0000.0138 (3)0.000
O10.0453 (8)0.0515 (9)0.0588 (10)0.0231 (7)0.0107 (7)0.0021 (7)
C10.0328 (9)0.0277 (8)0.0449 (10)0.0010 (7)0.0145 (8)0.0008 (7)
O20.0531 (9)0.0486 (8)0.0536 (9)0.0156 (7)0.0179 (7)0.0098 (7)
C20.0296 (9)0.0238 (8)0.0394 (10)0.0003 (6)0.0138 (8)0.0002 (7)
O30.0255 (9)0.0354 (9)0.0481 (11)0.0000.0068 (8)0.000
C30.0388 (10)0.0313 (9)0.0344 (9)0.0030 (7)0.0132 (8)0.0038 (7)
O40.0439 (11)0.0353 (9)0.0435 (11)0.0000.0262 (9)0.000
C40.0329 (9)0.0314 (8)0.0319 (9)0.0038 (7)0.0071 (7)0.0005 (7)
C50.0251 (8)0.0225 (7)0.0347 (9)0.0014 (6)0.0119 (7)0.0004 (6)
C60.0356 (10)0.0324 (9)0.0317 (9)0.0012 (7)0.0104 (8)0.0024 (7)
C70.0331 (9)0.0326 (9)0.0353 (9)0.0050 (7)0.0054 (8)0.0020 (7)
Geometric parameters (Å, º) top
S1—O31.4357 (18)C2—C31.389 (2)
S1—O41.4409 (19)C3—C41.384 (2)
S1—C5i1.7732 (16)C3—H30.9300
S1—C51.7732 (16)C4—C51.386 (2)
O1—C11.283 (2)C4—H40.9300
O1—H1A0.9040C5—C61.386 (2)
C1—O21.249 (2)C6—C71.381 (2)
C1—C21.490 (2)C6—H60.9300
C2—C71.386 (2)C7—H70.9300
O3—S1—O4120.27 (12)C4—C3—H3120.0
O3—S1—C5i108.31 (7)C2—C3—H3120.0
O4—S1—C5i107.57 (7)C3—C4—C5119.04 (16)
O3—S1—C5108.31 (7)C3—C4—H4120.5
O4—S1—C5107.57 (7)C5—C4—H4120.5
C5i—S1—C5103.59 (10)C6—C5—C4121.61 (15)
C1—O1—H1A118.3C6—C5—S1119.12 (13)
O2—C1—O1123.98 (16)C4—C5—S1119.24 (13)
O2—C1—C2119.79 (16)C7—C6—C5118.80 (16)
O1—C1—C2116.22 (16)C7—C6—H6120.6
C7—C2—C3120.21 (16)C5—C6—H6120.6
C7—C2—C1120.51 (16)C6—C7—C2120.39 (16)
C3—C2—C1119.21 (16)C6—C7—H7119.8
C4—C3—C2119.91 (16)C2—C7—H7119.8
Symmetry code: (i) x, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2ii0.901.742.6390 (19)172
Symmetry code: (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC14H10O6S
Mr306.29
Crystal system, space groupMonoclinic, P21/m
Temperature (K)293
a, b, c (Å)5.0019 (4), 23.3653 (17), 5.7871 (5)
β (°) 110.151 (3)
V3)634.94 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.21 × 0.13 × 0.10
Data collection
DiffractometerMercury CCD
Absorption correctionMulti-scan
PROGRAM? (Reference?)
Tmin, Tmax0.943, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
4922, 1493, 1287
Rint0.023
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.104, 1.13
No. of reflections1493
No. of parameters100
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.36

Computer programs: CrystalClear (Rigaku, 2000), CrystalClear, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2i0.901.742.6390 (19)171.8
Symmetry code: (i) x, y, z+1.
 

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